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

HRID 369358Notes

Reaction equation

HRID 369358 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 methanol (90 ml), and 47% hydrobromic acid (100 ml) was added to the solution under ice-cooling with stirring. After reaction for 16 hours at room temperature, water was added to the reaction mixture under ice-cooling with stirring, and the precipitates were collected by filtration and washed with water and hexane to give 2-bromo-4'-hydroxy-3'-hydroxymethylacetophenone (9.54 g) having a melting point of 117-119° C.

Workup

  1. temperaturecooling
  2. customAfter reaction for 16 hours at room temperature
  3. temperaturecooling
  4. stirringwith stirring
  5. filtrationthe precipitates were collected by filtration
  6. washwashed with water and hexane

Sources & evidence

ORD record
ord-cfb39df89f724af9b05e67f90861301d
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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