View source for Chemistry:Friedel–Crafts reaction

{{Short description|Set of reactions to attach substituents to an aromatic ring}}
{{Reactionbox
| Name = Friedel-Crafts reaction
| Type = Coupling reaction
| NamedAfter = Charles Friedel <br/> James Crafts
| Section3 = {{Reactionbox Identifiers
   | RSC_ontology_id = 0000369
 }}
|Section1={{Reactionbox Conditions
   | Reference =
   | Solvent = 
   | Catalyst = {{center|Strong lewis acid: {{br}} [[Chemistry:Zeolite|Zeolite]], AlCl<sub>3</sub>  }}
   | Temperature = 
}}|Reaction={{Reactionbox Reaction
   | Reactant1 = Aromatic Ring
   | Reactant2 = Alkyl Halide, Alcohol, Alkene or Alkyne
   | Reagent1= 
   | Product1 = Coupling Product
   | Sideproduct1 = 
}}}}
The '''Friedel–Crafts reactions''' are a set of [[Chemistry:Organic reaction|reactions]] developed by Charles Friedel and James Crafts in 1877 to attach substituents to an [[Chemistry:Aromatic hydrocarbon|aromatic ring]].<ref>Friedel, C.; Crafts, J. M. (1877) "Sur une nouvelle méthode générale de synthèse d'hydrocarbures, d'acétones, etc.," ''Compt. Rend.'', '''84''': [http://gallica.bnf.fr/ark:/12148/bpt6k30410/f1386.table 1392] & [http://gallica.bnf.fr/ark:/12148/bpt6k30410/f1444.table 1450].</ref> Friedel–Crafts reactions are of two main types: [[Chemistry:Alkylation|alkylation]] reactions and [[Chemistry:Acylation|acylation]] reactions. Both proceed by [[Chemistry:Electrophilic aromatic substitution|electrophilic aromatic substitution]].<ref>{{Cite journal |last=Price, C. C. |year=1946 |title=The Alkylation of Aromatic Compounds by the Friedel-Crafts Method |journal=Org. React. |volume=3 |page=1 |doi=10.1002/0471264180.or003.01 |isbn=0471264180}}</ref><ref>{{Cite journal |last=Groves, J. K. |year=1972 |title=The Friedel–Crafts acylation of alkenes |journal=Chem. Soc. Rev. |volume=1 |page=73 |doi=10.1039/cs9720100073}}</ref><ref>{{Cite journal |last=Eyley, S. C. |year=1991 |title=The Aliphatic Friedel–Crafts Reaction |journal=Compr. Org. Synth. |volume=2 |pages=707–731 |doi=10.1016/B978-0-08-052349-1.00045-7 |isbn=978-0-08-052349-1}}</ref><ref>{{Cite journal |last=Heaney, H. |year=1991 |title=The Bimolecular Aromatic Friedel–Crafts Reaction |journal=Compr. Org. Synth. |volume=2 |pages=733–752 |doi=10.1016/B978-0-08-052349-1.00046-9 |isbn=978-0-08-052349-1}}</ref> 
[[File:Friedel-Crafts_Equation_Overview.svg|center|frameless|561x561px]]

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== Alkylation ==
{{Reactionbox
| Name = Friedel-Crafts alkylation
| Type = Coupling reaction
| NamedAfter = Charles Friedel <br/> James Crafts
| Section3 = {{Reactionbox Identifiers
   | OrganicChemistryNamed = friedel-crafts-alkylation
   | RSC_ontology_id = 0000046
 }}
|Reaction={{Reactionbox Reaction
   | Reactant1 = [[Chemistry:Aromaticity|Aromatic Ring]]
   | Reactant2 =  [[Chemistry:Alkylation|Alkylating Agent]]
   | Reagent1= 
   | Product1 = Friedel-Crafts aromatic addition product
   | Sideproduct1 = HCl (reaction type dependent)
}}|Section1={{Reactionbox Conditions
   | Reference =
   | Solvent = 
   | Catalyst = {{center|Strong lewis acid: {{br}}[[Chemistry:Zeolite|Zeolite]], AlCl<sub>3</sub> }}
   | Temperature = 
}}}}

===With alkyl halides ===
Friedel–Crafts alkylation involves the [[Chemistry:Alkylation|alkylation]] of an aromatic ring.  Traditionally, the alkylating agents are alkyl halides. Many alkylating agents can be used instead of alkyl halides.  For example, [[Chemistry:Enone|enone]]s and [[Chemistry:Epoxide|epoxide]]s can be used in presence of protons. Traditionally also, the reaction employs a strong [[Chemistry:Lewis acid|Lewis acid]], such as [[Chemistry:Aluminium chloride|aluminium chloride]] as catalyst.<ref>{{Cite journal |last1=Rueping, M. |last2=Nachtsheim, B. J. |year=2010 |title=A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis |journal=Beilstein J. Org. Chem. |volume=6 |issue=6 |pages=6 |doi=10.3762/bjoc.6.6 |pmc=2870981 |pmid=20485588}}</ref>

This reaction suffers from the disadvantage that the product is more [[Chemistry:Nucleophile|nucleophilic]] than the reactant because alkyl groups are [[Chemistry:Electrophilic aromatic substitution#Reaction rate|activators for the Friedel–Crafts reaction]]. Consequently, overalkylation can occur. Steric hindrance can be exploited to limit the number of alkylations, as in the ''t''-butylation of 1,4-dimethoxybenzene.<ref>{{Cite book |last=L. |first=Williamson, Kenneth |title=Macroscale and microscale organic experiments |date=4 January 2016 |others=Masters, Katherine M. |isbn=9781305577190 |edition=Seventh |location=Boston, MA, USA |oclc=915490547}}</ref>

:[[File:Friedel-CraftsAlkylationStericProtection.png|350px|t-butylation of 1,4-dimethoxybenzene]]

Furthermore, the reaction is only useful for primary alkyl halides in an intramolecular sense when a 5- or 6-membered ring is formed.  For the intermolecular case, the reaction is limited to [[Chemistry:Tertiary carbon|tertiary]] alkylating agents, some secondary alkylating agents (ones for which carbocation rearrangement is degenerate), or alkylating agents that yield stabilized carbocations (e.g., benzylic or allylic ones).  In the case of primary alkyl halides, the carbocation-like complex (R<sup>(+)</sup>---X---Al<sup>(-)</sup>Cl<sub>3</sub>) will undergo a [[Chemistry:Carbocation|carbocation]] [[Chemistry:Rearrangement reaction|rearrangement reaction]] to give almost exclusively the rearranged product derived from a secondary or tertiary carbocation.<ref name="Smith2007" />

==== Mechanism ====
The general mechanism for primary alkyl halides is shown below.<ref name="Smith2007">{{March6th}}</ref>
:[[File:Friedel-Crafts-Alkylierung 2.svg|thumb|center|Mechanism of Friedel–Crafts alkylation.|390x390px]]For primary (and possibly secondary) alkyl halides, a carbocation-like complex with the Lewis acid, [R<sup>(+)</sup>---(X---MX''<sub>n</sub>'')<sup>(–)</sup>] is more likely to be involved, rather than a free carbocation.

===With Alkenes===
<!-- This section is linked from [[Chemistry:Cumene process|Cumene process]] -->
In commercial applications, the alkylating agents are generally [[Chemistry:Alkene|alkene]]s. Protonation of alkenes generates [[Chemistry:Carbocation|carbocation]]s, the electrophiles.  A laboratory-scale example by the synthesis of [[Chemistry:Neophyl chloride|neophyl chloride]] from benzene and [[Chemistry:Methallyl chloride|methallyl chloride]] using [[Chemistry:Sulfuric acid|sulfuric acid]] catalyst.<ref>{{OrgSynth | doi = 10.15227/orgsyn.032.0090 | year = 1952 | title = Neophyl Chloride | author1 =  Smith, W. T. Jr. |author2=Sellas, J. T.|volume=32|page=90}}</ref>
:[[File:Neophyl chloride synthesis.svg]]
Such alkylations are of major industrial importance, e.g. for the production of [[Chemistry:Ethylbenzene|ethylbenzene]], the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in [[Chemistry:Cumene process|cumene process]]:
:[[File:Benzene ethylation.svg]]
:[[File:Propylene+C6H6.svg|Alkylation of benzene with propylene in cumene process]]
Industrial production typically uses [[Chemistry:Solid acid|solid acid]]s derived from a [[Chemistry:Zeolite|zeolite]] as the catalyst.

===Friedel–Crafts dealkylation===
Friedel–Crafts alkylations can be [[Physics:Reversible reaction|reversible]] as illustrated by many [[Chemistry:Transalkylation|transalkylation]] reactions.<ref name="Tsai">Tsai, Tseng-Chang "Disproportionation and Transalkylation of Alkylbenzenes over Zeolite Catalysts". Elsevier Science, 1999</ref>
[[File:1,3-Diisopropylbenzene via transalkylation.svg|thumb|center|380 px|[[Chemistry:1,3-Diisopropylbenzene|1,3-Diisopropylbenzene]] is produced via transalkylation, a special form of Friedel–Crafts alkylation.]]

== Acylation ==
{{Reactionbox
| Name = Friedel-Crafts acylation
| Type = Coupling reaction
| NamedAfter = Charles Friedel <br/> James Crafts
| Section3 = {{Reactionbox Identifiers
 | OrganicChemistryNamed = friedel-crafts-acylation
 | RSC_ontology_id = 0000045
 }}
|Reaction={{Reactionbox Reaction
   | Reactant1 = [[Chemistry:Aromaticity|Aromatic Ring]]
   | Reactant2 =  [[Chemistry:Acylation|Acylating agents]]
   | Reagent1= 
   | Product1 = Friedel-Crafts aromatic addition product
   | Sideproduct1 = HCl (reaction type dependent)
}}|Section1={{Reactionbox Conditions
   | Reference =
   | Solvent = 
   | Catalyst = {{center|Strong lewis acid: {{br}} [[Chemistry:Zeolite|Zeolite]], AlCl<sub>3</sub>}}
   | Temperature = 
}}}}

Friedel–Crafts acylation involves the [[Chemistry:Acylation|acylation]] of aromatic rings. Typical acylating agents are [[Chemistry:Acyl chloride|acyl chloride]]s.  Acid anhydrides as well as carboxylic acids are also viable. A typical [[Chemistry:Lewis acid|Lewis acid]] catalyst is [[Chemistry:Aluminium trichloride|aluminium trichloride]].  Because, however, the product ketone forms a rather stable complex with Lewis acids such as AlCl<sub>3</sub>, a stoichiometric amount or more of the "catalyst" must generally be employed, unlike the case of the Friedel–Crafts alkylation, in which the catalyst is constantly regenerated.<ref>{{Cite journal |last1=Somerville |first1=L. F. |last2=Allen |first2=C. F. H. |date=1933 |title=β-Benzoylpropionic acid |journal=Organic Syntheses |volume=13 |page=12 |doi=10.15227/orgsyn.013.0012}}</ref> Reaction conditions are similar to the Friedel–Crafts alkylation. This reaction has several advantages over the alkylation reaction. Due to the electron-withdrawing effect of the carbonyl group, the [[Chemistry:Ketone|ketone]] product is always less reactive than the original molecule, so multiple acylations do not occur. Also, there are no [[Chemistry:Carbocation|carbocation]] rearrangements, as the acylium ion is stabilized by a resonance structure in which the positive charge is on the oxygen.

:[[File:Friedel-Crafts-acylation-overview.png|350px|Friedel–Crafts acylation overview]]

The viability of the Friedel–Crafts acylation depends on the stability of the acyl chloride reagent. Formyl chloride, for example, is too unstable to be isolated. Thus, synthesis of [[Chemistry:Benzaldehyde|benzaldehyde]] through the Friedel–Crafts pathway requires that formyl chloride be synthesized ''in situ''. This is accomplished by the Gattermann-Koch reaction, accomplished by treating benzene with [[Chemistry:Carbon monoxide|carbon monoxide]] and [[Chemistry:Hydrogen chloride|hydrogen chloride]] under high pressure, catalyzed by a mixture of [[Chemistry:Aluminium chloride|aluminium chloride]] and cuprous chloride. Simple ketones that could be obtained by Friedel–Crafts acylation are produced by alternative methods, e.g., oxidation, in industry.

=== Reaction mechanism ===
The reaction proceeds through generation of an acylium center.  The reaction is completed by deprotonation of the [[Chemistry:Arenium ion|arenium ion]] by AlCl<sub>4</sub><sup>−</sup>, regenerating the AlCl<sub>3</sub> catalyst.  However, in contrast to the truly catalytic alkylation reaction, the formed ketone is a moderate Lewis base, which forms a complex with the strong Lewis acid aluminum trichloride.  The formation of this complex is typically irreversible under reaction conditions.  Thus, a stochiometric quantity of AlCl<sub>3</sub> is needed.  The complex is destroyed upon aqueous workup to give the desired ketone.  For example, the classical synthesis of deoxybenzoin calls for 1.1 equivalents of AlCl<sub>3</sub> with respect to the limiting reagent, phenylacetyl chloride.<ref>{{Cite web |url=http://www.orgsyn.org/demo.aspx?prep=CV2P0156 |title=Desoxybenzoin |website=orgsyn.org |language=en |access-date=2019-01-26}}</ref> In certain cases, generally when the benzene ring is activated, Friedel–Crafts acylation can also be carried out with ''catalytic'' amounts of a milder Lewis acid (e.g. Zn(II) salts) or a Brønsted acid catalyst using the anhydride or even the carboxylic acid itself as the acylation agent.

:[[File:F-C acylation mechanism.png|frameless|400x400px]]

If desired, the resulting ketone can be subsequently reduced to the corresponding alkane substituent by either [[Chemistry:Wolff–Kishner reduction|Wolff–Kishner reduction]] or [[Chemistry:Clemmensen reduction|Clemmensen reduction]]. The net result is the same as the Friedel–Crafts alkylation except that rearrangement is not possible.<ref>[https://www.organic-chemistry.org/namedreactions/friedel-crafts-acylation.shtm Friedel-Crafts Acylation]. Organic-chemistry.org. Retrieved 2014-01-11.</ref>

==Hydroxyalkylation==
Arenes react with certain [[Chemistry:Aldehyde|aldehyde]]s and ketones to form the hydroxyalkylated products, for example in the reaction of the mesityl derivative of [[Chemistry:Glyoxal|glyoxal]] with benzene:<ref>{{Cite journal |last1=Fuson, R. C. |last2=Weinstock, H. H. |last3=Ullyot, G. E. |year=1935 |title=A New Synthesis of Benzoins. 2{{prime}},4{{prime}},6{{prime}}-Trimethylbenzoin |journal=J. Am. Chem. Soc. |volume=57 |issue=10 |pages=1803–1804 |doi=10.1021/ja01313a015}}</ref>

:[[File:FriedelCraftsHydroAlkylation.png|400px|Friedel–Crafts hydroxyalkylation]]

As usual, the aldehyde group is more reactive electrophile than the phenone.

==Scope and variations==
[[File:EthylbenzenePost2000route.svg|right|thumb|263x263px|Alkylation of benzene & ethylene, one of the largest scale reactions practiced commercially.]]
This reaction is related to several classic named reactions:
* The acylated reaction product can be converted into the alkylated product via a [[Chemistry:Clemmensen reduction|Clemmensen]] and Wolff-Kishner reductions.{{sfn|Smith|March|2001|p=1835}}
* The Gattermann–Koch reaction can be used to synthesize benzaldehyde from benzene.{{sfn|Smith|March|2001|p=745}}
* The Gatterman reaction describes arene reactions with hydrocyanic acid.<ref name=March>{{March6th|page=725}}</ref><ref>{{cite book |last1=Smith |first1=M.B.|last2=March|first2=J |title=March's Advanced Organic Chemistry |date=2001 |page=725|isbn=0-471-58589-0}}</ref>
* The Houben–Hoesch reaction describes arene reactions with nitriles.{{sfn|Smith|March|2001|p=732}}
* A reaction modification with an aromatic phenyl ester as a reactant is called the [[Chemistry:Fries rearrangement|Fries rearrangement]].
* In the [[Chemistry:Scholl reaction|Scholl reaction]] two arenes couple directly (sometimes called '''Friedel–Crafts arylation''').<ref name="Grzybowski">{{Cite journal |last1=Grzybowski |first1=M. |last2=Skonieczny |first2=K. |last3=Butenschön |first3=H. |last4=Gryko |first4=D. T. |year=2013 |title=Comparison of Oxidative Aromatic Coupling and the Scholl Reaction |journal=Angew. Chem. Int. Ed. |volume=52 |issue=38 |pages=9900–9930 |doi=10.1002/anie.201210238 |pmid=23852649}}</ref>
* In the [[Chemistry:Blanc chloromethylation|Blanc chloromethylation]] a chloromethyl group is added to an arene with formaldehyde, hydrochloric acid and zinc chloride.
* The '''Bogert–Cook synthesis''' (1933) involves the [[Chemistry:Dehydration reaction|dehydration]] and [[Chemistry:Isomerization|isomerization]] of ''1-β-phenylethylcyclohexanol'' to the octahydro derivative of [[Chemistry:Phenanthrene|phenanthrene]]<ref>This reaction with
[[Chemistry:Phosphorus pentoxide|phosphorus pentoxide]]: {{Cite journal |last1=Kamp |first1=J. V. D. |last2=Mosettig |first2=E. |year=1936 |title=Trans- and Cis-As-Octahydrophenanthrene |journal=Journal of the American Chemical Society |volume=58 |issue=6 |pages=1062–1063 |doi=10.1021/ja01297a514}}</ref>

[[File:Bogert-Cook Synthesis.png|500px]]

* The '''Darzens–Nenitzescu synthesis of ketones''' (1910, 1936) involves the acylation of [[Chemistry:Cyclohexene|cyclohexene]] with [[Chemistry:Acetyl chloride|acetyl chloride]] to methylcyclohexenylketone.
* In the related '''Nenitzescu reductive acylation''' (1936) a [[Chemistry:Saturated and unsaturated compounds|saturated]] [[Chemistry:Hydrocarbon|hydrocarbon]] is added making it a reductive acylation to methylcyclohexylketone
* The '''Nencki reaction''' (1881) is the ring acetylation of phenols with acids in the presence of zinc chloride.<ref>{{Cite journal |last1=Nencki, M. |last2=Sieber, N. |year=1881 |title=Ueber die Verbindungen der ein- und zweibasischen Fettsäuren mit Phenolen |url=https://zenodo.org/record/1427886 |journal=J. Prakt. Chem. |language=de |volume=23 |pages=147–156 |doi=10.1002/prac.18810230111}}</ref>
* In a [[Chemistry:Green chemistry|green chemistry]] variation [[Chemistry:Aluminium chloride|aluminium chloride]] is replaced by [[Chemistry:Graphite|graphite]] in an alkylation of [[Chemistry:P-Xylene|''p''-xylene]] with 2-bromobutane. This variation will not work with primary halides from which less carbocation involvement is inferred.<ref>{{Cite journal |last1=Sereda, Grigoriy A. |last2=Rajpara, Vikul B. |year=2007 |title=A Green Alternative to Aluminum Chloride Alkylation of Xylene |journal=J. Chem. Educ. |volume=2007 |issue=84 |page=692 |bibcode=2007JChEd..84..692S |doi=10.1021/ed084p692}}</ref>

===Dyes===
Friedel–Crafts reactions have been used in the synthesis of several [[Chemistry:Triphenylmethane|triarylmethane]] and [[Chemistry:Xanthene|xanthene]] dyes.<ref>{{Cite journal |last1=McCullagh |first1=James V. |last2=Daggett |first2=Kelly A. |year=2007 |title=Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions |url=https://pubs.acs.org/doi/abs/10.1021/ed084p1799 |journal=J. Chem. Educ. |volume=84 |issue=11 |page=1799 |bibcode=2007JChEd..84.1799M |doi=10.1021/ed084p1799 }}</ref> Examples are the synthesis of [[Chemistry:Thymolphthalein|thymolphthalein]] (a pH indicator) from two equivalents of [[Chemistry:Thymol|thymol]] and [[Chemistry:Phthalic anhydride|phthalic anhydride]]:

:[[File:ThymolphthaleinSynthesis.png|400px|Thymolphthalein synthesis]]

A reaction of phthalic anhydride with [[Chemistry:Resorcinol|resorcinol]] in the presence of [[Chemistry:Zinc chloride|zinc chloride]] gives the fluorophore [[Chemistry:Fluorescein|fluorescein]]. Replacing resorcinol by N,N-diethylaminophenol in this reaction gives [[Chemistry:Rhodamine B|rhodamine B]]:

:[[File:RhodamineBsynthesis.png|400px|Rhodamine B synthesis]]

===Haworth reactions===
The '''Haworth reaction''' is a classic method for the synthesis of 1-tetralone.<ref>{{Cite journal |last=Haworth, Robert Downs |year=1932 |title=Syntheses of alkylphenanthrenes. Part I. 1-, 2-, 3-, and 4-Methylphenanthrenes |journal=J. Chem. Soc. |page=1125 |doi=10.1039/JR9320001125}}</ref> In this reaction, [[Chemistry:Benzene|benzene]] is reacted with [[Chemistry:Succinic anhydride|succinic anhydride]], the intermediate product is reduced and a second FC acylation takes place with addition of acid.<ref>Li, Jie Jack (2003) [https://books.google.com/books?id=6mZJ3084ouAC&pg=PA175 ''Name Reactions: A Collection of Detailed Reaction Mechanisms''], Springer, {{ISBN|3-540-40203-9}}, p. 175.</ref>

:[[File:Haworth-reaction.svg|600px|Haworth reaction]]

In a related reaction, [[Chemistry:Phenanthrene|phenanthrene]] is synthesized from [[Chemistry:Naphthalene|naphthalene]] and succinic anhydride in a series of steps which begin with FC acylation.

:[[File:Haworth Phenanthrene synthesis.svg|600px|Haworth phenanthrene synthesis]]

===Friedel–Crafts test for aromatic hydrocarbons===
Reaction of [[Chemistry:Chloroform|chloroform]] with aromatic compounds using an [[Chemistry:Aluminium chloride|aluminium chloride]] catalyst gives triarylmethanes, which are often brightly colored, as is the case in triarylmethane dyes. This is a bench test for aromatic compounds.<ref>John C. Gilbert., Stephen F. Martin. Brooks/Cole CENGAGE Learning, 2011. pp 872. 25.10 Aromatic Hydrocarbons and Aryl Halides – Classification test. {{ISBN|978-1-4390-4914-3}}</ref>

==See also==
* [[Chemistry:Ethylene oxide#Alkylation of aromatic compounds|Ethylene oxide]]
* Friedel family, lineage of French scientists
* [[Chemistry:Hydrodealkylation|Hydrodealkylation]]
* [[Chemistry:Transalkylation|Transalkylation]]

==References==
<references/>

===Friedel–Crafts reactions published on ''Organic Syntheses''===
* Alkylations:
** {{OrgSynth|author1=Everett M. Schultz |author2=Sally Mickey|year=1949|title=Diphenylacetone|volume=29|page=38|url=http://www.orgsyn.org/Content/pdfs/procedures/CV3P0343.pdf}}
** {{OrgSynth|author1=Lee Irvin Smith|year=1930|title=Durene|volume=10|page=32|url=http://www.orgsyn.org/Content/pdfs/procedures/CV2P0248.pdf}}
** {{OrgSynth|author1=C. S. Marvel |author2=W. M. Sperry|year=1928|title=Benzophenone|volume=8|page=26|url=http://www.orgsyn.org/Content/pdfs/procedures/CV1P0095.pdf}} 
* Acylations:
** {{OrgSynth|author1=R. E. Lutz|year=1940|title=trans-dienzoethylene|volume=20|page=29|url=http://www.orgsyn.org/Content/pdfs/procedures/CV3P0248.pdf}}
** {{OrgSynth|author1=L. F. Fieser|year=1940|title=β-(3-Acenaphthoyl)Propionic acid|volume=20|page=1|url=http://www.orgsyn.org/Content/pdfs/procedures/CV3P0006.pdf}}
** {{OrgSynth|author1=C. F. H. Allen |author2=W. E. Barker|year=1932|title=Desoxybenzoin|volume=12|page=16|url=http://www.orgsyn.org/Content/pdfs/procedures/CV2P0156.pdf}}
** {{OrgSynth|author1=Kamil Paruch |author2=Libor Vyklicky |author3=Thomas J. Katz|year=2003|title=Preparation of 9,10-dimethoxyphenanthrene and 3,6-diacetyl-9,10-dimethoxyphenanthrene|volume=80|page=227|url=http://www.orgsyn.org/Content/pdfs/procedures/v80p0227.pdf}}
** {{OrgSynth|author1=Roger Adams |author2=C. R. Noller|year=1925|title=p-bromoacetophenone|volume=5|page=17|url=http://www.orgsyn.org/Content/pdfs/procedures/CV1P0109.pdf}}
** {{OrgSynth|author1=L. F. Fieser|year=1925|title=β-methyanthraquinone|volume=4|page=43|url=http://www.orgsyn.org/Content/pdfs/procedures/CV1P0353.pdf}}
** {{OrgSynth|author1=Perry C. Reeves|year=1977|title=Carboxylation of aromatic compounds: ferrocenecarboxylic acid|volume=56|page=28|url=http://www.orgsyn.org/Content/pdfs/procedures/CV6P0625.pdf}}

{{Alcohols}}
{{Organic reactions}}

{{DEFAULTSORT:Friedel-Crafts reaction}}
[[Category:Substitution reactions]]
[[Category:Carbon-carbon bond forming reactions]]

{{Sourceattribution|Friedel–Crafts reaction}}