Acetic Anhydride → 3-Cyclohexen-1-ol, 3,5,5-trimethyl-, acetate

HRID 436973Notes

Reaction equation

HRID 436973 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH2:10][C:8](=[O:9])[CH2:7][C:6]([CH3:12])([CH3:11])[CH:5]=1.CC1[CH2:15][CH:16]([OH:22])CC(C)(C)C=1.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>CO>[C:16]([O:9][CH:8]1[CH2:7][C:6]([CH3:12])([CH3:11])[CH:5]=[C:4]([CH3:3])[CH2:10]1)(=[O:22])[CH3:15]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 10108Beta-IsophoroneHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 112750493,5,5-Trimethylcyclohex-3-en-1-ol

Product 1

HCID 907913-Cyclohexen-1-ol, 3,5,5-trimethyl-, acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared by reduction by means of sodium borohydride in methanol of β-isophorone [obtained according to J. Am. Chem. Soc., 63, 2308 (1941)] and subsequent acetylation of the obtained 3,5,5-trimethyl-cyclohex-3-en-1-ol by means of acetic anhydride in the presence of sodium acetate at 50° C. during 20 hours.

Sources & evidence

ORD record
ord-8d0c2eaa33b341db8134d9877f64ba69
Source dataset
uspto-grants-1977_06
Patent number
US04029106

Reaction notes

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