Water → 2-Methoxyethyl alpha-(hydroxyimino)-2-phenylacetate

HRID 393135Notes

Reaction equation

HRID 393135 reaction equation
[C:1]1([C:7](=O)[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH:17][NH3+:18].C(OCC)(=O)C.O>N1C=CC=CC=1>[OH:17][N:18]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 134616742-Methoxyethyl 2-oxo-2-phenylacetateHCID 22029257Hydroxyammonium hydrochloride

Product 1

HCID 739911462-Methoxyethyl alpha-(hydroxyimino)-2-phenylacetateYield 102.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

61.7 g (0.296 mol) of 2-methoxyethyl phenylglyoxalate are dissolved in 360 ml pyridine. 22.7 g (0.0.326 mol) of hydroxylammonium hydrochloride are added in portions to this solution. When the addition is complete, the reaction mixture is stirred at room temperature for 2 hours. After addition of ethyl acetate and water, the organic layer is separated, washed with diluted HCl and water and dried over magnesium sulfate. Evaporation of the solvent gives 68 g (100%) of crude 2-methoxyethyl α-(hydroxyimino)-2-phenylacetate as a slightly brownish liquid. This compound is used without further purification in the next step.

Workup

  1. additionWhen the addition
  2. customthe organic layer is separated
  3. washwashed with diluted HCl and water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-153d0b723769488b82a655356e886643
Source dataset
uspto-grants-2004_10
Patent number
US06806024B1

Reaction notes

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