P-Chloroacetophenone → (1S)-1-(4-chlorophenyl)ethan-1-ol

HRID 324750

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1.CC(C1C=CC(Cl)=CC=1)=O.ClC1C=CC([C@H](O)C)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7467P-Chloroacetophenone

HCID 18825Benzenemethanol, 4-chloro-alpha-methyl-

HCID 643324(1R)-1-(4-chlorophenyl)ethan-1-ol

Product 1

HCID 6950175(1S)-1-(4-chlorophenyl)ethan-1-olYield 42%

Procedure

As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate (±)-1-(4-chlorophenyl)ethanol (200 mg) requires 8 days by going through bioconversion to 4-chloroacetophenone accompanying sterically selective oxidation of (R)-1-(4-chlorophenyl)ethanol to obtain 84 mg of (S)-1-(4-chlorophenyl)ethanol at a yield of 42%. Optical purity was obtained at 87% e.e.

Sources & evidence

ORD record: ord-91cd50917b1144c38183482da2f75132
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218581B1

Linked notes

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