Potassium Carbonate → methoxycarbonyl-1,4-benzoquinone

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.2 g (0.00119 mol) of methyl gentisate (14), 0.2 g (0.0014 mol) of potassium carbonate and 0.6 g (0.0026 mol) of silver oxide in 10 mL of benzene (freshly distilled) was stirred at 50° C. (bath temperature) under argon for 10 min under dark. The reaction mixture was cooled to room temperature, filtered through Celite, rinsed with small amount of ether, concentrated on a rotary evaporator and then under vacuum to give 0.198 g (100% yield) of methoxycarbonyl-1,4-benzoquinone (15); 1H NMR (CDCl3) d 7.13 (s, 1H, C3 H), 6.84 (s, 2H, C5,6 Hs), 3.92 (s, 3H, OMe). The proton NMR spectrum indicates the material is about 100% pure and is used in the next step without purification.

Provenance & Evidence