Water → 2-(6-Methoxy-2-naphthyl)propionic acid

Temperature

25 °C

A mixture of 2-bromo-1,1-dimethoxy-1-(6-methoxy-2-naphthyl)-propane (3.39 g; 10 mmol), calcium carbonate (1 g; 10 mmol), N,N-dimethylformamide (12 g) and of water (8 g) is heated at reflux under stirring for 7 h. The mixture is cooled to 25° C., added with diethyl ether (100 ml) and the insoluble is filtered. The resulting solution is washed with water and the solvent is removed in vacuo. The residue is added with 30% sodium hydroxide aqueous solution (10 ml) and with methanol (30 ml). The reaction mixture is refluxed for 2 h and then cooled to room temperature, the mixture is diluted with water (100 ml) and extracted with diethyl ether (2×30 ml). The aqueous phase is acidified with concentrated hydrochloric acid, the insoluble is filtered, washed with water and dried at 80° C. under vacuum to give 2-(6-methoxy-2-naphthyl)-propionic acid (2.18 g; 9.5 mmol; yield 95 %), m.p. 154°-155° C.

1. temperatureat reflux
2. filtrationthe insoluble is filtered
3. washThe resulting solution is washed with water
4. customthe solvent is removed in vacuo
5. additionThe residue is added with 30% sodium hydroxide aqueous solution (10 ml) and with methanol (30 ml)
6. temperatureThe reaction mixture is refluxed for 2 h
7. temperaturecooled to room temperature
8. additionthe mixture is diluted with water (100 ml)
9. extractionextracted with diethyl ether (2×30 ml)
10. filtrationthe insoluble is filtered
11. washwashed with water
12. customdried at 80° C. under vacuum

ORD record

ord-4d87ca80dfbc4e44822ebe1b91a27efe

Source dataset

uspto-grants-1986_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04618697