2-Methylbenzaldehyde → 2-(2-Methylphenyl)oxirane

Participants

Reaction Steps

Sodium hydride (57%) (4.84 g., 0.115 mole) previously washed with hexane was stirred with dry dimethylsulfoxide (70 ml) at 65°-70° for 2 hours under argon. The mixture was diluted with dry THF (70 ml), cooled to -5° and trimethylsulfonium iodide (23.5 g, 0.115 mole) in 100 ml of dry DMSO was added over a period of 3 minutes. After stirring for one minute o-tolualdehyde (11.5 g, 0.0926 mole) was added at a moderate rate while keeping the reaction mixture at 0° to -5°. The mixture was stirred at 0° for 5 minutes and at room temperature for 1 hour, diluted with 500 ml of ice water and extracted three times with ether. The ether solution was washed with saturated sodium chloride, dried with sodium sulfate and evaporated to an oil which was distilled under reduced pressure (~0.25-0.50 mm) to give 10.25 g (83 %) of o-methylstyrene oxide as a clear liquid (b.p. 35°-38°).

Provenance & Evidence