Acetophenone → 1-Phenylethanol, (R)-

HRID 1890139Notes

Reaction equation

HRID 1890139 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+]>C(O)(C)C>[CH3:2][C@@H:1]([OH:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 6375161-Phenylethanol, (R)-Yield 93.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An autoclave was charged with acetophenone (1.03 Kg), isopropanol (300 g), and KOH (100 g, 10 M). Catalyst R-XylPPhos RuCl2 R-DAIPEN (150 g) was then added, and the reaction mixture was hydrogenated at a pressure of 30 bar and a temperature of 70° C. for 12 hours. The resultant mixture was transferred into a separatory funnel The aqueous layer was discarded. The organic layer was washed with water (200 ml) and distilled first at 100 mmHg to remove isopropanol, and then at 5-10 mmHg to provide (R)-alpha-methylbenzyl alcohol (980 g).

Workup

  1. washThe organic layer was washed with water (200 ml)
  2. distillationdistilled first at 100 mmHg
  3. customto remove isopropanol

Sources & evidence

ORD record
ord-40e4fd49c56340ef973c5857ab4a9173
Source dataset
uspto-grants-2013_08
Patent number
US08506943B2

Reaction notes

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