Vinyl Acetate → 1-Phenylethanol, (S)-

HRID 982306Notes

Reaction equation

C([O:4][CH:5]=[CH2:6])(=O)C.[CH3:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>>[C:9]1([C@@H:5]([OH:4])[CH3:6])[CH:8]=[CH:7][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 7904Vinyl Acetate

HCID 8058Hexane

Product 1

HCID 4431351-Phenylethanol, (S)-Yield 85%

Conditions

Temperature: 25 °C

Procedure

(R, S)-1-phenylethanol (0.276 gram, 2 mmol) and vinyl acetate (0.17 gram, 2 mmol) were dissolved in 10 ml of n-hexane dried in advance on Molecular Sieve 4A for one day. To the resulting solution was added 1 gram of PPL (porcine pancrea lipase: Product of Sigma), and the mixture was stirred at 25° C. and 150 r.p.m. to give (S)-1-phenylethanol in an optical purity of 90% with a theoretical yield of 85%.

Workup

dry with materialdried in advance on Molecular Sieve 4A for one day
additionTo the resulting solution was added 1 gram of PPL (porcine pancrea lipase: Product of Sigma)

Sources & evidence

ORD record: ord-6a87f6606ebd40bab1308f52e0bad9d1
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04996158

Reaction notes

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