Sodium Hydroxide → Dimethyl Sulfate

Participants

Reaction Steps

Preparation of 9-anthryl n-butyl methyl sulfonium trifluoromethanesulfonate, wherein trifluoromethanesulfonate and triflate are synonymous and R1 was n-butyl, R2 was methyl, X- was CF3 (CF2)nSO3-, and n was 0. A solution of 25.0 g (129 millimoles (mM)) of anthrone, 32.5 g (24.4 milliliters (mL), 257 mM) of dimethylsulfate, and 0.5 g of benzyl triethylammonium chloride was prepared in 250 mL of dichloromethane and 100 mL of water. Next, 80 g (1 M) of 50% sodium hydroxide was dripped into this solution with rapid stirring. GC analysis of the reaction immediately after the addition determined essentially complete conversion to 9-methoxyanthracene. After stirring for 1 hour the water layer was discarded, the organic layer washed with 5% aqueous HCl, then saturated sodium bicarbonate, dried with magnesium sulfate, then evaporated to give a faintly yellow solid. The solid was then recrystallized from heptane to give 9-methoxyanthracene.

Provenance & Evidence