The stereoselective reaction of the Grignard reagent derived from menthyl chloride with halohydrocarbon has been studied. The reaction yielded menthyl compound and neomenthyl compound, and the main product was menthyl compound. The stereoselectivity was relactive to the activity of halohydrocarbon. The poorer the activity of halohydrocarbon, the better the stereoselectivity. The de of the reaction of active benzyl chloride was 27.9% , that of less active α-bromostyrene and 2-bromopropene were more than 91% and that of bromobenzene and dichloromethane came to 100%.

Key words: menthyl chloride, Grignard reagent, halohydrocarbon, reactivity, stereoselectivity