Ethanone, 2-chloro-1-(3-chlorophenyl)- → 2-Chloro-1-(3-chloro-phenyl)-ethanol

HRID 2180344Notes

Reaction equation

HRID 2180344 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)=[O:4].C(O)=O.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 168006Ethanone, 2-chloro-1-(3-chlorophenyl)-HCID 11084032Triethylammonium formate

Product 1

HCID 114695632-Chloro-1-(3-chloro-phenyl)-ethanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-3′-chloroacetophenone (94.5 mg; 0.5 mmol) and a formic acid/triethylamine azeotropic mixture (0.1 ml) were added to a solution of chloro(pentamrethylcyclopentadienyl)iridium (III) (1R,2R)-N-(p-toluenesulfonyl)-1,2-diaminocyclohexane (3.5 mg, 0.0005 mmol, s/c=100) in ethyl acetate (0.5 ml), followed by stirring at room temperature for 16 hours. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography to give a desired compound, (+)-2-chloro-1-(3′-chlorophenyl)ethanol (88.5 mg; yield: 92.7%; optical purity: 91.0%).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dec2abbc7dd54059bad2f694da1c1f72
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

Loading…