Hydroxylamine → 6-(4-Chlorophenylsulfanyl)-hexa-2,4-dienoic acid hydroxyamide

Participants

Reaction Conditions

Reaction Steps

To a solution of the 6-(4-chlorophenylsulfanyl)-hexa-2,4-dienoic acid methyl ester (0.44 g, 1.64 mmol) in distilled THF (9.0 mL) containing 50% aqueous hydroxylamine (1.0 ml, 15.2 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1M, 2.6 mL, 2.6 mmol) over a period of 30 minutes. After stirring at 0° C. for 1 h, distilled water (9.0 mL) was added and the mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C. The aqueous solution was extracted with ethyl acetate (3×30 mL) and the combined extracts were dried over anhydrous MgSO4, and evaporated to dryness. The residue was recrystallised from acetone to give the title compound (0.21 g, 48%) as a pale brown powder, mp 120-122° C. (decomp).

Provenance & Evidence