3,5-Di-tert-butylsalicylaldehyde

3,5-Di-tert-butylsalicylaldehyde

IUPAC name 3,5-Di-tert-butyl-2-hydroxybenzaldehyde
Identifiers
CAS number	37942-07-7^N
PubChem	688023
ChemSpider	599518^Y
ChEMBL	CHEMBL427197^Y
Jmol-3D images	Image 1
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^Y Key: RRIQVLZDOZPJTH-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₁₅H₂₂O₂
Molar mass	234.33 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

References

^ ^a ^b 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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v75p0001 ; Coll. Vol. 10: 96