Reacción #1483

Ecuación de reacción

(±)6-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthlene

TsOH

water

→

title compound

3,4-Dihydro-4,4-dimethyl-1-(carboethoxymethyl)-6-acetyl-naphthalene

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas periodically removed by a Dean-Stark trap
2. 2
   OtroThe solvent was removed
3. 3
   Otrothe residue was purified by column chromatography (silica, ethyl acetate/hexane (1/3))

Procedimiento

A solution of (±)6-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthlene ((Compound D16, 321 mg, 0.90 mmol) and catalytic amount of TsOH in 20 ml of benzene was refluxed for 12 h. During the reaction the water generated from the reaction was periodically removed by a Dean-Stark trap. The solvent was removed and the residue was purified by column chromatography (silica, ethyl acetate/hexane (1/3)) to give the title compound as an oil (215 mg).

Fuente