Reacción #575310

Ecuación de reacción

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

potassium hydroxide

hydrochloric acid

→

titled compound

Rendimiento 102.8%

(E)-3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-2-methylpropenoic acid

Rendimiento 102.8%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby refluxing for 1 hour
2. 2
   Extracciónfollowed by extraction with ethyl acetate
3. 3
   LavadoThe organic layer was washed with brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Otroevaporated
6. 6
   workup.ADDITIONDiisopropyl ether was added to the resultant residue
7. 7
   Filtraciónthe resultant crystals were filtered

Procedimiento

28 g of ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate was dissolved in 240 ml of ethanol and a potassium hydroxide aqueous solution (potassium hydroxide 28 g/water 55 ml) was added, followed by refluxing for 1 hour. 280 ml of 2N hydrochloric acid was added to the reaction mixture at ice bath temperature to make it acidic, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Diisopropyl ether was added to the resultant residue and the resultant crystals were filtered to obtain 23 g of the titled compound as pale yellow crystals.

Fuente