Synthesis
A mixture of 16.3 g (0.132 moles) 45percent potassium hydroxide solution, 21.5 g (0.125 moles) of 3-amino-4-chlorobenzoic acid, 100 g of xylene, 40/3 g (0.132 moles) of 1-bromohexadecane and 4.5 g of benzyltriethylammonium bromide (10 mol percent) was heated to reflux. Water was removed using a Dean-Stark trap. After 3 hr at reflux (115-120° C.), the reaction was judged complete by tic. The reaction was cooled to 90° C. and washed with water to remove salts. The solvent was removed on a roto-vap, and the residue was crystallized from heptane to give 40.7 g (83 per cent yield) of a solid Hexadecyl 3-amino-4-chlorobenzoate.
