Acetone → 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)

Participants

Reaction Steps

18.6 g of the 1,2,4,5-tetrahydroxybenzene prepared according to Example 4 (0.13 mole) and 70 ml acetone (58.6 g, 1.0 mole) was dissolved in 1 1 tetrahydrofuran. 168 g P2O5 (1.18 mole) was added to the vigorously stirred mixture in portions as fast as possible. The mixture was heated to reflux for 4 hours. After cooling to room temperature the solids were filtered with suction and washed with 0.5 L ether. The combined filtrates were treated with 10 g K2CO3 and stirred 1 hour, filtered and evaporated to dryness yielding a yellow-brown oily solid. The product was triturated with petroleum ether, decanted and evaporated to yield 13.8 g of the title compound (48%) as white-yellow crystals, mp=122° C., which can be recrystalized from a small amount of petroleum ether.

Provenance & Evidence