Methanol → 2-bromo-1-(2-hydroxy-phenyl)-ethanone O-methyl-oxime

HRID 612811Notes

Reaction equation

HRID 612811 reaction equation
[Br:1][CH:2](O)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.Cl.[CH3:13][O:14][NH2:15].C[OH:17]>>[CH3:13][O:14][N:15]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:17])[CH2:2][Br:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 222371692-Bromo-2-hydroxy-1-phenylethan-1-one

Product 1

HCID 1359803292-bromo-1-(2-hydroxy-phenyl)-ethanone O-methyl-oximeYield 52%

Conditions

Temperature
0 °C

Procedure

107.5 g (0.5 mol) of ω-bromo-2-hydroxy-acetophenone in 500 ml of methanol together with 41.75 g (0.5 mol) of O-methylhydroxylamine hydrochloride are heated under reflux for 4 hours. The methanol is distilled off under reduced pressure and the residue is admixed with 500 ml of water and extracted with 4 times 100 ml of ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. At 0° C. , the residue is stirred with petroleum ether, affording 74 g (52% of theory) of crystalline 2-bromo-1-(2-hydroxy-phenyl)-ethanone O-methyl-oxime as a mixture of two stereoisomers (53% of isomer B and 33% of isomer A).

Workup

  1. temperatureunder reflux for 4 hours
  2. distillationThe methanol is distilled off under reduced pressure
  3. extractionextracted with 4 times 100 ml of ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-3ee08129f065433d838fca38966f2c19
Source dataset
uspto-grants-1999_12
Patent number
US06005104

Reaction notes

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