Acetophenone → 1-Phenylethanol, (R)-

HRID 2085538Notes

Reaction equation

HRID 2085538 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H][H]>CC(O)C>[C:4]1([C@H:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7410Acetophenone2×HCID 178418361HCID 178418361, compound

Product 1

HCID 6375161-Phenylethanol, (R)-Yield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Chiral hydrogenation of acetophenone was carried out (see formula (7) below). That is, a reaction was carried out in accordance with the procedures of Example 4 using the (S,SS)-ruthenium hydride complex (1.5 mg; 0.00125 mmol) synthesized in Example 2 and using acetophenone (150 mg; 1.25 mmol) as the substrate and 2-propanol (1.5 mL) as the solvent. However, the hydrogen pressure was set to 1 atmosphere, the reaction temperature was set to 25° C., and the reaction time was set to 12 hours. As a result, (R)-1-phenylethanol was obtained at a conversion rate of 99%, isolation yield of 95% (293 mg; 1.19 mmol), and enantiomeric excess of 97%.

Workup

  1. customsynthesized in Example 2
  2. customwas set to 25° C.

Sources & evidence

ORD record
ord-e59b269c060a4125811aca70567b42c9
Source dataset
uspto-grants-2004_04
Patent number
US06720439B1

Reaction notes

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