2-Chloroacetophenone → 2-Chloro-1-phenylethanol

HRID 2180324Notes

Reaction equation

HRID 2180324 reaction equation
C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.C(O)(C)C.CC(C)([O-])C.[K+].[Cl:37][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40]>C(O)(C)C>[Cl:37][CH2:38][CH:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[OH:40]

Participants

5

Reactant 3

HCID 107572-ChloroacetophenoneHCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideHCID 86592054potassium t-butoxide IPA

Product 1

HCID 928982-Chloro-1-phenylethanolYield 93.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of di-μ-chlorodichlorobis(pentamethylcyclopentadienyl)dirhodium (III) (155 mg, 0.025 mmol) and (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (36.6 mg, 0.1 mmol) in isopropyl alcohol (25.0 ml) was heated at 80° C. for 20 minutes while stirring. After cooling the solution to room temperature, a 0.1 M potassium tert-butoxide isopropyl alcohol solution (2.5 ml, 0.25 mmol) and an isopropyl alcohol solution (22.5 ml) of 2-chloroacetophenone (773.0 mg, 5.0 mmol) as a reaction substrate were added thereto, followed by stirring at room temperature for 14 hours. After completion of the reaction, the solvent was removed by evaporation, and the residue was purified by silica gel column chromatography to give a desired compound, (+)-2-chloro-1-phenylethanol (732.9 mg; yield: 93.6%; optical purity: 97.5% ee).

Workup

  1. additionsubstrate were added
  2. stirringby stirring at room temperature for 14 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by evaporation
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e6836328bc2f47d6ba61f38d22343888
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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