Dimethyl Sulfate → 4-(2',5'-Dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.0 g of 4-(2',5'-dihydroxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol, 40 ml of methylene chloride, 6 ml of water, 5.6 g of sodium hydroxide, 0.6 g of potassium carbonate, 1.6 g of dimethyl sulphate and 0.25 g of tert.butylammonium bromide is stirred well at 30° C. under argon for 3 hours and thereafter poured into water. The aqueous mixture 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 (3.7 g) there are obtained by column chromatography (silica gel, diethyl ether/n-hexane) 1.6 g of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol in the form of white crystals, m.p. 87°-88° C.

Provenance & Evidence