Reaction #1157211

Reaction equation

methyl phenylglyoxylate

hydroxylamine hydrochloride

triethylamine

→

methyl E-2-hydroxyimino-2-phenylacetate

Yield 13.0%

Solvents

methanol

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated
2. 2
   workup.ADDITIONthe residue was diluted with water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe ethyl acetate layer was washed with water, (MgSO4),
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residual crystals were recrystallized from ethyl acetate-hexane

Procedure

A mixture of methyl phenylglyoxylate (25.5 g), hydroxylamine hydrochloride (11.3 g), triethylamine (22.8 ml) and methanol (300 ml) was stirred for 17 hours at 60° C. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, (MgSO4), and then concentrated. The residual crystals were recrystallized from ethyl acetate-hexane to obtain methyl E-2-hydroxyimino-2-phenylacetate (3.58 g, yield 13%) as colorless crystals. m.p. 151-153° C.

Source