Acetophenone → 1-Phenylethanol, (S)-
Reaction equation
C([O-])=O.[Na+].[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])[CH3:6]>C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.C(O)=O>[C:8]1([C@@H:5]([OH:7])[CH3:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 30 °C
Procedure
Culture fluid was obtained by cultivating E. coli HB101 (pNCMFT) in a similar manner to Example 9. In a 100-mL portion of the culture fluid, 2.8 g of sodium formate, 3 mg of NAD+, and 10 g of acetophenone were added, and the mixture was stirred at 30° C. for 20 hours while controlling the pH of the reaction mixture to 6.0 with 5 N aqueous formic acid, which was added dropwise to the mixture. After the reaction, the reaction mixture was extracted with toluene, and combined organic layer was dried over anhydrous sodium sulfate. Removal of sodium sulfate, and evaporation of organic solvents from the organic layer under reduced pressure yielded 9.8 g of (S)-phenylethanol. The product (S)-phenylethanol was analyzed in accordance with the [Analysis condition (1) for gas chromatography] as described above, and found that the optical purity of the product was 99.9% e.e. or higher.
Workup
- customCulture fluid was obtained
- additionwas added dropwise to the mixture
- customAfter the reaction
- extractionthe reaction mixture was extracted with toluene
- dry with materialwas dried over anhydrous sodium sulfate
- customRemoval of sodium sulfate, and evaporation of organic solvents from the organic layer under reduced pressure
Sources & evidence
- ORD record
- ord-834ada1d353f418aa1c560a7175cf1ea
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129163B2
Reaction notes
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