Hydrogen Bromide → 2-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-one

HRID 367330Notes

Reaction equation

HRID 367330 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][Br:13])=[CH:7][C:6]=1[CH2:15][O:16]C(=O)C)(=O)C.Br.O>CO>[Br:13][CH2:12][C:11]([C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[C:6]([CH2:15][OH:16])[CH:7]=1)=[O:14]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 112788962-Acetoxy-5-(2-bromoacetyl)benzyl acetate

Product 1

HCID 113340552-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-oneYield 68.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetoxymethyl-4-bromoacetylphenyl acetate (18.6 g) was dissolved in 90 ml of methanol, 100 ml of 47% hydrobromic acid was added with stirring under ice-cooling, and the mixture was subjected to 16 hours of reaction at room temperature. Water was added to the reaction solution with stirring under ice-cooling, and the resulting precipitates were collected by filtration and washed with water and hexane to give 9.54 g of 2-bromo-4'-hydroxy-3'-hydroxymethylacetophenone having a melting point of 117 to 119° C.

Workup

  1. temperaturecooling
  2. customthe mixture was subjected to 16 hours of reaction at room temperature
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. customthe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water and hexane

Sources & evidence

ORD record
ord-e86e760ef26a46c2a17e06cc180d55e1
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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