Reaction #2044997

Reaction equation

sulphuric acid

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

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

methanol

→

6

Yield 89.5%

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

Yield 89.5%

Conditions

Workup

1. 1
   Temperaturerefluxed for 6 hours
2. 2
   workup.DISTILLATIONMethanol (1000 ml) was distilled off
3. 3
   Otherthe cooled reaction mass
4. 4
   workup.ADDITIONwas poured onto ice water (3000 ml)
5. 5
   FiltrationCrude 6 was filtered
6. 6
   Otherdried
7. 7
   Otherrecrystallised from a mixture of ethyl acetate:hexane (1:5)

Procedure

To a solution of methanol (2100 ml) and sulphuric acid (84 ml) was added 2-(6-Hydroxynaphthalen-2-yl)-propionic acid 5 (420 g, 1.944 mmol), and refluxed for 6 hours. Methanol (1000 ml) was distilled off and the cooled reaction mass was poured onto ice water (3000 ml). Crude 6 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 6 (400 g, 89.5%) as a white fluffy powder. The melting point found to be 89.5-92° C. The structure was confirmed with IR and NMR.

Source