Hydrochloric Acid → HCID 11054797, compound

Participants

Reaction Steps

A mixture of 2-(3-bromophenyl)-2-(hydroxyimino)acetonitrile (19.0 g), 4N aqueous solution of potassium hydroxide (100 ml) and 2-methoxyethanol (100 ml) was heated under reflux for 4 hours. The reaction mixture was cooled to room temperature, 1N hydrochloric acid was added to make the solution acidic and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in ethanol (200 ml) and concentrated sulfuric acid (catalytic amount) was added. The reaction mixture was heated under reflux for 48 hours, cooled to room temperature, poured into an aqueous saturated solution of sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl Z-2-(3-bromophenyl)-2-(hydroxyimino)acetate (3.31 g, yield 14%) as a pale-brown oil from an ethyl acetate-hexane (1:3, v/v)-eluted fraction.

Provenance & Evidence