Water → HCID 136127060, compound

HRID 432053Notes

Reaction equation

HRID 432053 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]([O:11][CH3:12])=[O:10].[CH3:14][O:15][NH3+:16].[Cl-].O>CO>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:16][O:15][CH3:14])[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 11639O-methylhydroxylammonium chlorideHCID 182159Benzeneacetic acid, 2-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 136127060HCID 136127060, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.4 g (0.0533 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 92.4%, log p=1.87) from process step 2 and 7.4 g (0.089 mol) of 0-methylhydroxylamine hydrochloride in 150 ml of methanol are boiled under reflux for three hours. The reaction mixture is poured into water, the product is extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 8.2 g of crude product which, according to HPLC, contains 17.2% methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 65.4% methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.38.

Workup

  1. temperatureunder reflux for three hours
  2. extractionthe product is extracted with diethyl ether
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-39f053a2bb5249da8703107218e8f589
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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