Reacción #575320

Ecuación de reacción

ethyl (E)-3-(3-methoxy-4-methoxymethoxy-5-propyl-1-naphthyl)-2-methylpropenoate

→

titled compound

Rendimiento 37.4%

(Z)-3-(4-hydroxy-3-methoxy-5-propyl-1-naphthyl)-2-methylpropenoic acid

Rendimiento 37.4%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroirradiated with light from a high pressure mercury lamp through a Pyrex
2. 2
   Filtraciónfilter for 2.5 hours
3. 3
   ConcentraciónThe reaction mixture was concentrated in vacuo
4. 4
   Otropurified by silica gel column chromatography (3% ethyl acetate/hexane)

Procedimiento

196.5 g of ethyl (E)-3-(3-methoxy-4-methoxymethoxy-5-propyl-1-naphthyl)-2-methylpropenoate was dissolved in 2.6 liters of acetone and irradiated with light from a high pressure mercury lamp through a Pyrex filter for 2.5 hours. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (3% ethyl acetate/hexane) to obtain 59.2 g of the titled compound as a pale yellow oil. At the same time, 136.4 g of a mixture of the E and Z isomers was recovered.

Fuente