1-[(4-METHOXYPHENYL)METHYL]-CYCLOPROPANECARBOXYLIC ACID synthesis

Yield:-

Reaction Conditions:

Stage #1: cyclopropropanecarbonitrilewith sodium hydroxide;waterHeating / reflux;
Stage #2: with hydrogenchloride in water; pH=5;

Steps:

16

1- (4-methoxy-benzyl)-cyclopropanecarboxylic acid; The crude 1- (4-methoxybenzyl)- cyclopropanecarbonitrile was refluxed in sodium hydroxide (10% aqueous solution, 30 mL) overnight. The mixture was diluted with water (30 mL) and then washed with ethyl ether. The aqueous phase was acidified with 2 M hydrochloric acid to pH 5 and extracted three times with ethyl acetate (50 mL). The combined organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give the pure product. (5. 6 g, 54.4% from cyclopropanecarbonitrile). ESI-MS m/z calc. 206.1, found; 206.9 (M+1) 1H NMR (DMSO): 8 : 12.15 (s, 1 H), 7.13 (d, J = 8.4, 2 H), 6. 80 (d, J = 8. 4,2 H), 3.69 (s, 3 H), 2.78 (s, 2 H), 1.07-1. 04 (m, 2 H), 0.76-0. 74 (m, 2 H)

References:

WO2005/75435,2005,A1 Location in patent:Page/Page column 147-148