Sodium Carbonate → 3(2H)-Benzofuranone, O-methyloxime

HRID 612808Notes

Reaction equation

HRID 612808 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH2:5]Br.C(=O)([O-])[O-].[Na+].[Na+]>COC(C)(C)C.O>[CH3:1][O:2][N:3]=[C:4]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH2:5]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 1359803292-bromo-1-(2-hydroxy-phenyl)-ethanone O-methyl-oxime

Product 1

HCID 542716163(2H)-Benzofuranone, O-methyloximeYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

74 g (0.303 mol) of 2-bromo-1-(2-hydroxy-phenyl)-ethanone O-methyl-oxime are dissolved in 350 ml of tert-butyl methyl ether and heated under reflux with a solution of 40 g (0.377 mol) of sodium carbonate in 400 ml of water with vigorous stirring for 5 days. The organic phase is separated off and dried over sodium sulphate and the solvent is distilled off under reduced pressure, affording 45.5 g (82.8% of theory, 90% of Z isomer according to HPLC analysis) of crude benzofuran-3-one O-methyl-oxime.

Workup

  1. temperatureheated
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-09c6ffaae91b440d8fc77429aff08908
Source dataset
uspto-grants-1999_12
Patent number
US06005104

Reaction notes

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