Reacción #1106680

Ecuación de reacción

hydrochloric acid

Catechol

sodium methoxide

methyl dichloroacetate

→

benzo[1,3]dioxole-2-carboxylic acid methyl ester

Disolventes

Water

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was heated
2. 2
   Temperaturato reflux overnight
3. 3
   Extracciónthe mixture was extracted with diethyl ether (3×100 mL)
4. 4
   SecadoThe combined organic solution was dried with MgSO4
5. 5
   Concentraciónconcentrated to a brown solid
6. 6
   Otrochromatographed (2% ethyl acetate in hexane)

Procedimiento

Catechol (10.26 g, 93.2 mmol), sodium methoxide (25% by weight in methanol, 40.3 g, 186 mmol), and methyl dichloroacetate (13.3 g, 93.2 mmol) were combined in dry methanol (100 mL). The solution was heated to reflux overnight. The reaction was cooled to room temperature, acidified by addition of concentrated hydrochloric acid and then reduced in volume under vacuum to about 50 mL. Water was added and the mixture was extracted with diethyl ether (3×100 mL). The combined organic solution was dried with MgSO4, concentrated to a brown solid, and chromatographed (2% ethyl acetate in hexane) to yield benzo[1,3]dioxole-2-carboxylic acid methyl ester as a colorless oil.

Fuente