View source for Chemistry:3,5-Di-tert-butylsalicylaldehyde

{{DISPLAYTITLE:3,5-Di-''tert''-butylsalicylaldehyde}}
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 477217700
| Name = 3,5-Di-''tert''-butylsalicylaldehyde
| ImageFileL1 = 3,5-Di-tert-butylsalicylaldehyde.svg
| ImageFileR1 = 3,5-Di-tert-butylsalicylaldehyde powder from crystals.jpg
| PIN = 3,5-Di-''tert''-butyl-2-hydroxybenzaldehyde
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 37942-07-7
| CASNo_Ref = {{cascite|changed|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KQA2N5HW8Z
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 427197
| PubChem = 688023
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 599518
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C15H22O2/c1-14(2,3)11-7-10(9-16)13(17)12(8-11)15(4,5)6/h7-9,17H,1-6H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RRIQVLZDOZPJTH-UHFFFAOYSA-N
| SMILES = O=Cc1cc(cc(c1O)C(C)(C)C)C(C)(C)C
| InChI = InChI=1S/C15H22O2/c1-14(2,3)11-7-10(9-16)13(17)12(8-11)15(4,5)6/h7-9,17H,1-6H3
  }}
|Section2={{Chembox Properties
| C=15 | H=22 | O=2
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt =
  }}
}}

'''3,5'-Di-''tert''-butylsalicylaldehyde''' is an organic compound. It is a pale yellow solid. This aldehyde is a building block for preparing salen ligands.

==Preparation==
This compound is commercially available. It may be prepared by the [[Chemistry:Duff reaction|Duff reaction]], from 2,4-di-''tert''-butylphenol and [[Chemistry:Hexamethylenetetramine|hexamethylenetetramine]]:<ref name = jacobsen>{{OrgSynth | title = (R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst | author = Jay F. Larrow and Eric N. Jacobsen | collvol = 10 | collvolpages = 96 | year = 2004 | prep = v75p0001}}</ref>

:[[File:Duff reaction.svg|300px]]

==Reactions==
Condensation of this aldehyde with various diamines gives various salen ligands, which are popular for [[Chemistry:Catalysis|catalysis]]. For example, the enantiopure ligand for [[Chemistry:Jacobsen's catalyst|Jacobsen's catalyst]] may be prepared from the appropriate [[Chemistry:Trans-1,2-Diaminocyclohexane|1,2-diaminocyclohexane]]. The catalyst is obtained by further reaction with [[Chemistry:Manganese(II) acetate|manganese(II) acetate]] and atmospheric oxygen in the presence of a chloride source.<ref name=jacobsen/>

:[[File:Synthesis of (R,R)-Jacobsen's catalyst.png|525px]]

==References==
<references/>

{{DEFAULTSORT:Di-tert-butylsalicylaldehyde, 3,5-}}
[[Category:Hydroxybenzaldehydes]]
[[Category:Tert-butyl compounds]]

{{Sourceattribution|3,5-Di-tert-butylsalicylaldehyde}}