Reacción #2492374

Ecuación de reacción

2-(6-Methoxycarbonylmethoxy-naphthalen-2-yl)-propionic acid methyl ester

hydrochloric acid

→

89

Rendimiento 71.9%

2-(6-Carboxymethoxy-naphthalen-2-yl)-propionic acid

Rendimiento 71.9%

Disolventes

NaOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mass was cooled to room temperature
2. 2
   FiltraciónCrude 89 was filtered
3. 3
   Otrodried
4. 4
   Otrorecrystallized from a mixture of ethyl acetate:hexane (1:6)

Procedimiento

A mixture of 2-(6-Methoxycarbonylmethoxy-naphthalen-2-yl)-propionic acid methyl ester 31 (23 grams, 76.16 mmol) in 4 N—NaOH solutions (230 mL) was heated on a water bath at 90° C. for 8 hours. The reaction mass was cooled to room temperature and the pH adjusted to 2 with concentrated hydrochloric acid. Crude 89 was filtered, dried, and recrystallized from a mixture of ethyl acetate:hexane (1:6) to give pure 89 (15 grams, 71.9%) as a white powder. Mp: 185-188° C. IH NMR (DMSO-d6) δ 1.54(d,3H,CH3), 3.80(q,1H,CH), 4.74(s,2H,OCH2), 7.08(s,1H,Ar), 7.22(m,1H,Ar), 7.42(m,1H,Ar), 7.66(m,3H,Ar).

Fuente