7-(benzyloxy)-2-naphthoic acid synthesis

Yield:188904-08-7 72%

Reaction Conditions:

Stage #1: 7-benzyloxy-2-naphthonitrilewith potassium hydroxide;water in ethanol;toluene at 80; for 72 h;
Stage #2: with hydrogenchloride in ethanol;water;toluene;

Steps:

5

KOH (406 mg, 7.3 mmol) is added to a suspension of 7-benzyloxy-2-naphthonitrile (626 mg; 2.42 mmol) in water, ethanol, and toluene (15 mL, 1:3:2). The reaction is heated to 80° C. for 72 hours. The reaction is allowed to cool, poured into 1M HCl and extracted three times with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and concentrated to dryness. The product is purified by column chromatography (step gradient, 5 to 10% methanol in CH2Cl2). The resulting material is crystallized from ethanol-water to give 7-benzyloxy-2-naphthoic acid (484 mg, 72%) as a white solid. HRMS (EI) calculated for C18H14O3: 278.0943, found 278.0947.

References:

US2003/236270,2003,A1 Location in patent:Page 40