3-(2,5-DICHLORO-PHENOXYMETHYL)-BENZOIC ACID synthesis

Yield:438466-28-5 88%

Reaction Conditions:

Stage #1: methyl 3-[(2,5-dichlorophenoxy)methyl]benzoatewith water;sodium hydroxide in methanol at 50;
Stage #2: with hydrogenchloride in methanol;water;

Steps:

1.2

(2) 3-[(2,5-dichlorophenoxy)methyl]benzoic acid To a solution of methyl 3-[(2,5-dichlorophenoxy)methyl]benzoate (13.5 g), obtained in the above-mentioned reaction, in methanol (300 mL) was added 4N aqueous sodium hydroxide solution (100 mL), and the mixture was stirred at 50° C. overnight. After cooling, 6N hydrochloric acid (80 mL) was added, and the resulting precipitate was collected by filtration and dried to give the object product (11.3 g, 88%) as a white solid. ¹H NMR (300 MHz, DMSO-d₆) δ ppm 5.33 (s, 2H) 7.05 (dd, J=2.7, 8.7 Hz, 2H) 7.37 (d, J=2.4 Hz, 1H) 7.47-7.58 (m, 2H) 7.70 (d, J=7.5 Hz, 1H) 7.92 (d, J=7.5 Hz, 1H) 8.06 (s, 1H)

References:

US2009/325956,2009,A1 Location in patent:Page/Page column 22