Reacción #214326

Ecuación de reacción

hydrochloric acid

catechol

ethyl chloroacetate

→

1,4-benzodioxan-2-one

Rendimiento 61.3%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   workup.ADDITIONis added
3. 3
   workup.STIRRINGwith stirring
4. 4
   LavadoThe organic layer is washed twice with a minimum amount of water
5. 5
   workup.DISTILLATIONThe toluene is distilled off under reduced pressure
6. 6
   Otroto afford 119 grams of crude product
7. 7
   OtroRecrystallization from ethanol

Procedimiento

To a stirred solution of 120 grams of catechol and 10 grams of Aliquat® 336 (brand of tricaprylmethylammonium chloride, of General Mills Chemical Company of Minneapolis, Minnesota) at 80° C. is added ethyl chloroacetate (87 grams, 1 mole) over a one hour period. The reaction mass is stirred for one hour and then cooled. 1000 ml of dilute (5%) hydrochloric acid is added with stirring. The aqueous layer is discarded. The organic layer is washed twice with a minimum amount of water. The toluene is distilled off under reduced pressure to afford 119 grams of crude product. Recrystallization from ethanol afforded 92 grams of 1,4-benzodioxan-2-one.

Fuente