Acetophenone → 1-Phenylethanol, (S)-

HRID 2085539Notes

Reaction equation

HRID 2085539 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 4431351-Phenylethanol, (S)-Yield 97%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Chiral hydrogenation of acetophenone was carried out (see formula (8) below). That is, a reaction was carried out in accordance with the procedures of Example 4 using the (R,RR)-ruthenium hydride complex (45.3 mg; 0.0425 mmol) synthesized in Example 1 and using acetophenone (102.1 g; 0.85 mol) as the substrate and 2-propanol (100 mL) as the solvent. However, the hydrogen pressure was set to 10 atmosphere, the reaction temperature was set to 22˜41° C., and the reaction time was set to 14 hours. As a result, (S)-1-phenylethanol was obtained at a conversion rate of 99.8%, isolation yield of 97% (100.7 g; 0.82 mol), and enantiomeric excess of 81%.

Workup

  1. customsynthesized in Example 1
  2. customwas set to 22˜41° C.

Sources & evidence

ORD record
ord-0dd9b8f119f84f8186c96923269b1ba0
Source dataset
uspto-grants-2004_04
Patent number
US06720439B1

Reaction notes

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