Acetoacetic Acid → HCID 57026684, compound

HRID 1197510Notes

Reaction equation

HRID 1197510 reaction equation
[CH:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC([CH2:17][C:18]([OH:20])=[O:19])=O.[C:21]([O:24]C(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[CH:8]1([CH2:7][C:1]2[C@@H:2]([O:20][C:18](=[O:19])[CH3:17])[C@@H:3]([O:24][C:21](=[O:23])[CH3:22])[CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 96Acetoacetic AcidHCID 7918Acetic AnhydrideHCID 20444Benzene, (cyclohexylmethyl)-

Product 1

HCID 57026684HCID 57026684, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound is prepared by the microbial oxidation of cyclohexylmethylbenzene (W. Korte et al. J. Org. Chem. 39, 1168-70 (1974)) by Pseudomonas putida 39D using the method of T. Hudlicky et al. J. Am. Chem. Soc. 110, 4735-41 (1988) and D. Gibson et al. Biochemistry, 9, 1626-30 (1970) followed by protection as the diacetate using acetic anhydride in pyridine.

Sources & evidence

ORD record
ord-62a2d5ce38274989841c78679a1a9563
Source dataset
uspto-grants-1994_01
Patent number
US05275950

Reaction notes

Loading…