Hydrochloric Acid → HCID 14676200, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-hydroxy-1,2-dihydro-3-naphthoic acid (1 g), potassium carbonate (5 g), potassium iodide (2.5 g), N,N-dimethylformamide (30 ml) and methoxy ethyl bromide (2 ml) is stirred for 12 hours at 100° C. After cooling, water (300 ml) and ethyl acetate (200 ml) are added to the reaction mixture, and the mixture is shaken thoroughly. The organic layer is separated, washed with water, dried and evaporated under reduced pressure. the residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1) to give a colorless oily product, which is dissolved in methanol (50 ml). To the solution is added an aqueous solution (10 ml) of sodium hydroxide (2 g). The mixture is left standing for one hour, and then acidified with hydrochloric acid, followed by addition of water (300 ml). The resulting precipitates are collected by filtration and recrystallized from a mixture of methanol and water to give 7-methoxyethoxy-1,2-dihydro-3-naphthoic acid (0.65 g) as colorless needles, m.p. 122°-127° C.

Provenance & Evidence