Hydrochloric Acid → HCID 178448044, compound

Participants

Reaction Steps

0.12 g of magnesium shavings were covered with 5 ml of absolute diethyl ether while gassing with nitrogen and then, after the addition of a crystal of iodine, covered with a solution of 1.3 g of 4-(trifluoromethoxy)benzyl bromide in 25 ml of diethyl ether. After completion of the addition the mixture was heated to reflux for a further 30 minutes. The reaction mixture was transferred into a dropping funnel and then added dropwise at 0° C. and while gassing with nitrogen to a solution of 0.9 g of 3E-[trans-4-(trans-4-[1E-propenyl]cyclohexyl)cyclohexyl]-allyl pivalate, 0.03 g of copper-(I) chloride and 25 ml of absolute diethyl ether. After completion of the addition the reaction mixture was stirred at room temperature for a further 30 minutes, then treated with 20 ml of 25% hydrochloric acid and the organic phase was separated. The aqueous phase was extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed in succession with 500 ml of water, 250 ml of concentrated potassium carbonate solution and again with 500 ml of water, dried over magnesium sulphate, filtered and subsequently concentrated. The residue was purified by chromatography on silica gel with hexane. Recrystallization from acetone gave 0.5 g of pure 1-trifluoromethoxy-4-[4E-(trans-4-(trans-4-[1E-propenyl]cyclohexyl)cyclohexyl)-3-butenyl]benzene with m.p. (C-N) 63° C. and cl.p. (N-1) 149° C.

Provenance & Evidence