4'-Methoxyacetophenone → (1R)-1-(4-methoxyphenyl)ethan-1-ol

HRID 324757

Reaction equation

HRID 324757 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1.CC(C1C=CC(OC)=CC=1)=O.COC1C=CC([C@@H](O)C)=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 74764'-MethoxyacetophenoneHCID 1011481-(4-Methoxyphenyl)ethanolHCID 6950190(S)-1-(4-Methoxyphenyl)ethanol

Product 1

HCID 641443(1R)-1-(4-methoxyphenyl)ethan-1-olYield 48%

Procedure

As shown here, the biochemical conversion reaction of immobilized soy bean protein for the substrate (±)-1-(4-methoxyphenyl)ethanol (200 mg) requires 5 days by going through bioconversion to 4-methoxyacetophenone accompanying sterically selective oxidation of (S)-1-(4-methoxyphenyl)ethanol to obtain 96 mg of (R)-1-(4-methoxyphenyl)ethanol at a yield of 48%. Optical purity was obtained at 97% e.e.

Sources & evidence

ORD record
ord-102329e520d947d0bf5486ad1bb158dc
Source dataset
uspto-grants-2001_04
Patent number
US06218581B1

Linked notes

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