Catechol → SBB059257

Participants

Reaction Steps

A vigorously agitated mixture of 220 grams (2 gram-mols) of catechol, 2000 ml. of water, 80 grams (2 gram-mols) of sodium hydroxide and 143 grams (1 grammol) of bis(beta-chloroethyl)ether is reacted at reflux at 102°-103°C. for 16 hours under nitrogen. It is then acidified with concentrated hydrochloric acid. When unreacted bis(2-chloroethyl)ether and 1000 ml. of water have been removed by distillation, the mixture separates into two layers. The organic layer is recovered and treated with 700 ml. of methanol and chilled with ice water. The crystals that subsequently form are filtered off, washed with cold methanol, and dried. The 2,2'-(oxydiethylenedioxy)-diphenol product, 67 to 74 grams (23 to 25.5% yield), melts at 85°C. and analyzes as follows (a typical example.

Provenance & Evidence