Reacción #1482

Ecuación de reacción

ethylene glycol

3,4-dihydro-4,4-dimethyl-7-acetyl-naphthalen-1(2H)-one

p-toluenesulfonic acid monohydrate

3,4-dihydro-4,4-dimethyl-6-acetyl-naphthalen-1(2H)-one

→

title compound

6-(2-methyl-1,3-dioxolan-2-yl)-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting solution was heated
2. 2
   Temperaturato reflux for 18 h
3. 3
   Concentraciónconcentrated under reduced pressure

Procedimiento

A solution of 1.80 g (8.34 mmol) of a 1:5 mixture of 3,4-dihydro-4,4-dimethyl-7-acetyl-naphthalen-1(2H)-one (Compound D14a); and 3,4-dihydro-4,4-dimethyl-6-acetyl-naphthalen-1(2H)-one (Compound D14b) in 50 mL benzene was combined with 517.7 mg (8.34 mmol) of ethylene glycol and 20.0 mg (0.11 mmol) of p-toluenesulfonic acid monohydrate. The resulting solution was heated to reflux for 18 h, cooled to room temperature, and concentrated under reduced pressure. The title compound was isolated by column chromatography (10% EtOAc-hexanes) as a colorless oil.

Fuente