Boron trifluoride etherate → HCID 18609528, compound

Participants

Reaction Steps

5.0 g of (E)-4-(2',5'-diacetoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenyl acetate are dissolved in 50 ml of methanol and treated with 0.2 g of boron trifluoride etherate. The mixture is boiled at reflux for 4 hours, then cooled to room temperature and poured into aqueous sodium bicarbonate solution. The aqueous solution is extracted with diethyl ether, and the ether phase is washed in sequence with sodium bicarbonate solution and sodium chloride solution, dried over anhydrous sodium sulphate and evaporated to dryness. From the residue (4.6 g) there are obtained by column chromatography (silica gel, diethyl ether/n-hexane/methanol) 4.0 g of (E)-4-(2',5'-diacetoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol in the form of white crystals, m.p. 118°-120° C.

Provenance & Evidence