Reacción #83001

Ecuación de reacción

3,4-epoxy-1-butene

acetic anhydride

triethylamine

acetic acid

→

3,4-diacetoxy-1-butene

Rendimiento 87.0%

Disolventes

diglyme

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe autoclave was purged with nitrogen twice
2. 2
   workup.WAITGC analysis of the crude mixture after 2 hrs revealed

Procedimiento

A 300-mL autoclave was charged with 40 mL (0.50 mol) of 3,4-epoxy-1-butene, 62.2 g (0.61 mol) acetic anhydride, 1.8 g (0.018 mol) of triethylamine, 1.1 g (0.018 mol) acetic acid and 4.2 mL of diglyme. The autoclave was purged with nitrogen twice, then the vessel was pressurized to 8 bars (100 psig) with nitrogen. The agitator was started and an initial sample was taken. The mixture was heated to 125° C. During the course of 2 hrs, samples were taken every 15 min for analysis by GC. GC analysis of the crude mixture after 2 hrs revealed an 87% yield of 3,4-diacetoxy-1-butene with an 89% selectivity and 1.8% 3,4-epoxy-1-butene. The reaction was observed to be first order in 3,4-epoxy-1-butene with a first order rate constant of 0.024 min-1 (Table A). This example demonstrates the catalytic effect of the tertiary amine with acetic acid as the co-catalyst (Table B).

Fuente