2-Chloroacetophenone → 2-Chloro-1-phenylethanol

HRID 1954233Notes

Reaction equation

HRID 1954233 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>O1CCCC1>[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 928982-Chloro-1-phenylethanolYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-chloroacetophenone (5 g, 0.032 mol), sodium borohydride (6.1 g, 0.16 mol) in tetrahydrofuran (30 ml) was allowed to stir at 60° C. for 18 hours. The reaction was quenched by water (200 ml) and stirred for another 2 hours. The mixture was extracted with methylene chloride (3×100 ml) and washed with water (3×150 ml). The organic layer was dried over sodium sulfate and filtered. The solvent was removed under vacuum and afforded 5.07 g(100%) of product as a clear oil. MS EI m/e 156 (M+).

Workup

  1. customThe reaction was quenched by water (200 ml)
  2. stirringstirred for another 2 hours
  3. extractionThe mixture was extracted with methylene chloride (3×100 ml)
  4. washwashed with water (3×150 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-8ea77367035144a188264657ff74f3fc
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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