Réaction #1960518

Équation de réaction

methanol

sulphuric acid

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

→

product

Rendement 89.5%

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

Rendement 89.5%

Solvants

hexane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was refluxed for 6 Hours
2. 2
   workup.DISTILLATIONMethanol (1000 ml) was distilled
3. 3
   Autrethe cooled reaction mass
4. 4
   workup.ADDITIONwas poured onto ice water
5. 5
   Autreto yield crude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester which
6. 6
   Filtrationwas filtered
7. 7
   Autredried
8. 8
   Autrerecrystallized
9. 9
   workup.ADDITIONa mixture of ethyl acetate

Mode opératoire

To a solution of methanol (2100 ml) and sulphuric acid (84 ml) was added 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid (420 grams). The reaction mixture was refluxed for 6 Hours. Methanol (1000 ml) was distilled, and the cooled reaction mass was poured onto ice water to yield crude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester which was filtered, dried and recrystallized using a mixture of ethyl acetate:hexane to yield pure product (400 grams, 89.5% yield) as a white fluffy powder with a melting point of 89.5-92° C. The pure product was characterized using 1H NMR spectroscopy in CDCl3 δ 1.60 (d, 3H, CH3), 3.70 (s, 3H, Ester), 3.88 (q, 1H, CH), 5.36 (bs, 1H, OH), 7.08 (m, 2H, Ar), 7.48 (m, 1H, Ar), 7.65 (m, 3H, Ar).

Source