Catechol → 1,3-Benzodioxole

Participants

Reaction Steps

A solution of 110 g. of catechol, 160 g. of 50 percent aqueous sodium hydroxide, and 100 ml. of DMSO was stirred and heated to 95°-100° C. for 15 minutes. The temperature of the solution was maintained in the same range while the solution was added over a period of 30 minutes to a refluxing solution of 100 ml. of methylene dichloride in 400 ml. of DMSO. After the addition, the temperature of the refluxing reaction mixture reached 120° C., and was maintained at this level for 2.5 hours. Following the same isolation procedures as indicated in (A) above, 99.7 g. (80 percent) of methylenedioxybenzene was isolated.

Provenance & Evidence