Reacción #1969507

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