Water → 2-Hydroxy-1-phenyl-1-propanone

HRID 732176Notes

Reaction equation

HRID 732176 reaction equation
Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C([O-])=[O:13].[Na+].O>CO>[OH:13][CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 164522-BromopropiophenoneHCID 2723810Sodium Formate

Product 1

HCID 1011212-Hydroxy-1-phenyl-1-propanoneYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-1-phenylpropan-1-one (6.0 g, 28.2 mmol) in methanol (50 mL) was added sodium formate (7.66 g, 113 mmol) and the mixture was heated under reflux for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to give the title compound (2.66 g, yield 63%) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d6f2cffbc2c446959ac9f5bbfcb664fc
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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