Reaction #2045058

Reaction equation

2-(6-Methoxycarbonylmethoxynaphthalen-2-yl)propionic acid methyl ester

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

HCl

→

96

Yield 71.9%

2-(6-Carboxymethoxynaphthalen-2-yl)propionic acid

Yield 71.9%

Solvents

NaOH

Conditions

Workup

1. 1
   TemperatureThe reaction mass was cooled to room temp.
2. 2
   FiltrationCrude 96 was filtered
3. 3
   Otherdried
4. 4
   Otherrecrystallised from a mixture of ethyl acetate:hexane (1:6)

Procedure

2-(6-Methoxycarbonylmethoxynaphthalen-2-yl)propionic acid methyl ester 7 (23 g, 76.16 mmol) in 4 N aqueous NaOH (230 ml) was heated on a water bath at 90° C. for 8 hrs. The reaction mass was cooled to room temp. and the pH adjusted to 2 with con. HCl. Crude 96 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to give pure 96 (15 g, 71.9%) as a white powder. Mp: 185-188° C.

Source