56 m 2h 3 37 s 3h esms calcd c 17 h 25 cl 2 no 5 393 1 found 394 2 m h a suspension of methyl 4 bis 2 39 chloroethyl amino 3 2 39 2 34 methoxyethoxy ethoxy benzoate 3 0 g 7 64 mmol in concentrated hcl 37 w w in h 2 o 50 ml was heated to refluxing under n 2 for 2 hours the reaction mixture was treated with ice h 2 o 100 ml extracted with chloroform 2 u00d7 100 ml the organic extract was concentrated to give methyl 4 bis 2 39 chloroethyl amino 3 2 39 2 34 methoxyethoxy ethoxy benzoic acid as a white solid 2 8 g 97 1 h nmr 300 mhz cdcl 3 7 68 dd j 8 4 2 1 hz 1h 7 55 d j 2 1 hz 1h 6 92 d j 8 7 hz 1h 4 22 m 1h 3 89 m 2h 3 67 m 10h 3 62 m 2h 3 39 s 3h esms calcd for c 16 h 23 cl 2 no b 5 379 1 found 408 2 m h a slurry of methyl 3 hydroxy 4 nitrobenzoate 5 5 g 0 028 mol iodooctane 10 0 g 0 042 mol and potassium carbonate 20 g in 100 ml dmf was stirred at 100 u00b0 c for 3 hours the reaction mixture was cooled to room temperature diluted with 500 ml h 2 o then extracted with ether ethyl acetate 9 1 2 u00d7 200 ml the combined organic solution was washed with 400 ml h 2 o dried over sodium sulfate and concentrated to form methyl 4 nitro.