p-Nitroacetophenone → (R)-1-(4-nitrophenyl)ethanol

HRID 324752

Reaction equation

HRID 324752 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:12])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].CC(C1C=CC([N+]([O-])=O)=CC=1)=O.[N+](C1C=CC([C@@H](O)C)=CC=1)([O-])=O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C@H:10]([OH:12])[CH3:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 7487p-NitroacetophenoneHCID 5923761-(4-Nitrophenyl)ethan-1-olHCID 9815318(1S)-1-(4-nitrophenyl)ethan-1-ol

Product 1

HCID 9793932(R)-1-(4-nitrophenyl)ethanolYield 38%

Procedure

As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate (±)-1-(4-nitrophenyl)ethanol (200 mg) requires 4 days by going through bioconversion to 4-nitroacetophenone accompanying sterically selective oxidation of (S)-1-(4-nitrophenyl)ethanol to obtain 76 mg of (R)-1-(4-nitrophenyl)ethanol at a yield of 38%. Optical purity was obtained at 54% e.e. HPLC conditions were set at a flow rate of 0.5 ml/min, while GC conditions were set to an oven temperature of 190° C.

Sources & evidence

ORD record
ord-75d1154ef2104dab9d1ede9d228ef9c2
Source dataset
uspto-grants-2001_04
Patent number
US06218581B1

Linked notes

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