Acetophenone → 1-Phenylethanol, (R)-

HRID 1452998Notes

Reaction equation

HRID 1452998 reaction equation
[OH-].[K+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4]>CC(O)C>[C:6]1([C@H:3]([OH:5])[CH3:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 6375161-Phenylethanol, (R)-Yield 99%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Into a pressure-resistant vessel was placed 11.1 mg (0.012 mmol) of RuCl2(DPEphos){(S,S)-DPEN} synthesized in Example 4, and then thereto were added 48 μl (0.024 mmol) of a 0.5M solution of potassium hydroxide in 2-propanol and 3.3 ml of 2-propanol. Under an argon atmosphere, the solution was stirred for 30 minutes. Thereafter, 350 μl (3.0 mmol) of acetophenone was added thereto, and then the solution was stirred under hydrogen atmosphere of 0.8 MPa (8 atm) for 4 hours to give (1R)-1-phenylethanol, which is an alcohol reductant of acetophenone, in a GC yield of not less than 99% and an asymmetric yield of 91% ee.

Workup

  1. customInto a pressure-resistant vessel was placed
  2. stirringthe solution was stirred under hydrogen atmosphere of 0.8 MPa (8 atm) for 4 hours

Sources & evidence

ORD record
ord-eefcb18815d745539d733043d1372235
Source dataset
uspto-grants-2009_01
Patent number
US07473793B2

Reaction notes

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