3,5-Di-tert-butylsalicylaldehyde

3,5-Di-*tert*-butylsalicylaldehyde
Names
	Preferred IUPAC name 3,5-Di-tert-butyl-2-hydroxybenzaldehyde
Identifiers
CAS Number	37942-07-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL427197 ;
ChemSpider	599518 ;
ECHA InfoCard	100.157.837
PubChem CID	688023;
CompTox Dashboard (EPA)	DTXSID80350777 ;
	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 Key: RRIQVLZDOZPJTH-UHFFFAOYSA-N ; 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;
	SMILES O=Cc1cc(cc(c1O)C(C)(C)C)C(C)(C)C;
Properties
Chemical formula	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

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 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]

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References

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, 10, p. 96

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[jacobsen-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, 10, p. 96