Reaction #1960517

Reaction equation

Naproxen

→

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

Yield 81.0%

Solvents

HBr

Conditions

Workup

1. 1
   Temperaturewas refluxed for 10 Hours
2. 2
   workup.ADDITIONpoured onto ice water (3000 ml)
3. 3
   FiltrationCrude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid was filtered
4. 4
   Otherdried
5. 5
   Otherrecrystallised from a mixture of ethyl acetate and hexane

Procedure

A mixture of Naproxen (500 grams) and 48% HBr solution (1500 ml) was refluxed for 10 Hours, poured onto ice water (3000 ml), and stirred for 30 minutes. Crude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid was filtered, dried and recrystallised from a mixture of ethyl acetate and hexane to give pure 2-(6-hydroxy-naphthalen-2-yl)-propionic acid (380 grams, 81%) as a white powder with a melting point of 186-188° C.

Source