615 ml and 1m naoh 246 ml was stirred at room temperature for 16 h the reaction mixture was concentrated under reduced pressure to 200 ml and then the reaction mixture was extracted with ethyl acetate 300 ml u00d7 2 the organic layers were combined and washed with water brine and dried with anhydrous na 2 so 4 the mixture was filtered and concentrated to afford the title compound as clear brown oil a suspension of ethyl 4 aminobenzate 10 0 g in methylene chloride 250 ml and triethylamine 17 5 ml was treated with benzoyl chloride at 0 u00b0 c allowed to warm to room temperature and stirred for 16 h the reaction mixture was diluted with water 300 ml and extracted with methylene chloride 200 ml u00d7 2 the organic layers were washed with water brine and dried with anhydrous na 2 so 4 the mixture was filtered and concentrated the residue was dissolved in hot diethyl ether then cooled to 0 u00b0 c the title compound was isolated after filtration of the diethyl ether solution 1 h nmr 400 mhz cdcl 3 u03b4 ppm 8 09 d j 8 8 hz 2h 7 98 s 1h 7 94 7 89 m 2h 7 77 d j 8 8 hz 2h 7 64 7 60 m 1h 7 57 7 52 m 2h 4.