Ethanol → Mepronil

Participants

Reaction Steps

A 22.7 g 0.1 mol) portion of 3'-hydroxy-2-methylbenzanilide was dissolved in 100 ml of 1N-potassium hydroxide solution. To this solution 150 ml of ethanol was added and the mixture was stirred for one hour, which was followed by the addition of 12.3 g (0.1 mol) of isopropylbromide. After the addition of the iso-propylbromide, the reaction mixture was warmed and stirred under reflux for 4 hours. After distillation of most of the ethanol, the oily material remaining was extracted with benzene and the residue was distilled to obtain 20.9 g (77.9%) of a red, viscous oil having a boiling point of 186° C/0.08 mm Hg. The product was recrystallized from a mixture of benzene and n-hexane (1 : 1) as white prismatic crystals having a melting point of 92° C. IR cm-1 (KBr-tablet) νNH 3250(S), νCH 2980(S), νCO 1660 (S), 1610(S).

Provenance & Evidence