3,5-Di-tert-butylsalicylaldehyde

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.

3,5-Di-tert-butylsalicylaldehyde
Names
Preferred IUPAC name
3,5-Di-tert-butyl-2-hydroxybenzaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.157.837
UNII
  • 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 checkY
    Key: RRIQVLZDOZPJTH-UHFFFAOYSA-N checkY
  • 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
  • O=Cc1cc(cc(c1O)C(C)(C)C)C(C)(C)C
Properties
C15H22O2
Molar mass 234.339 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

This compound is commercially available. It may be prepared by the Duff reaction, from 2,4-di-tert-butylphenol and hexamethylenetetramine:[1]

Reactions

Condensation of this aldehyde with various diamines gives various salen ligands, which are popular for catalysis. For example, the enantiopure ligand for Jacobsen's catalyst may be prepared from the appropriate 1,2-diaminocyclohexane. The catalyst is obtained by further reaction with manganese(II) acetate and atmospheric oxygen in the presence of a chloride source.[1]

References
  1. Jay F. Larrow and Eric N. Jacobsen (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Organic Syntheses.; Collective Volume, vol. 10, p. 96
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