Acetophenone → 1-Phenylethanol, (R)-

HRID 1751899Notes

Reaction equation

HRID 1751899 reaction equation
C([O-])=O.[K+].[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])[CH3:6]>[Ru].CO>[C:8]1([C@H:5]([OH:7])[CH3:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 7410AcetophenoneHCID 2735122Potassium Formate

Product 1

HCID 6375161-Phenylethanol, (R)-Yield 100%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A ruthenium complex RuCl[(R,R)-Tsdpen] (p-cymene) (6.4 mg, 0.01 mmol), potassium formate (1.0 g, 12 mmol) and acetophenone (1.20 g, 10 mmol, substrate/catalyst ratio=1000) were set in a 20 mL glass Schlenk-type reaction tube under an argon atmosphere. Methanol (6 mL) was added thereto and stirred at 50° C. for 24 hours to give (R)-1-phenylethanol at 100% yield and 96.2% ee optical purity.

Sources & evidence

ORD record
ord-d511fc8da28643ddb86b418f93f165e7
Source dataset
uspto-grants-2015_10
Patent number
US09162934B2

Reaction notes

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