Hydrochloric Acid → HCID 23468930, compound

Participants

Reaction Steps

16.4 g (0.05 mol) of 3-(2,3-dimethyl-7-bromo-5-benzofuranyl)-1,5-pentanediol are dissolved in 200 ml of pyridine. The solution is cooled to -8° to -10° and 8.5 ml (=12.6 g, 0.11 mol) of methanesulfonyl chloride are added dropwise at this temperature in the course of 30 minutes. The reaction mixture is allowed to react at -8° to -10° for 11/2 hours and is then poured onto 500 g of ice and the pH value is adjusted to about 1 by adding 5 N hydrochloric acid. This acid mixture is extracted 3 times with methylene chloride and the extracts are washed twice with 2 N hydrochloric acid and 3 times with water. The combined extracts are dried over sodium sulfate and the solvent is evaporated off under a waterpump vacuum. A crude product which crystallises spontaneously and has a melting point of 154°-156° is thereby obtained. Recrystallisation from methylene chloride/hexane gives 3-(2,3-dimethyl-7-bromo-5-benzofuranyl)-1,5-pentanediyl dimethanesulfonate as white crystals of melting point 158°-159°.

Provenance & Evidence