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With potassium hydroxide; benzyltriethylammonium bromide In water; xylene at 115 - 120℃; for 3 h;
Example 5; n-Hexadecyl-3-amino-4-chlorobenzoate: 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 mole percent) were heated to reflux and water was removed by means of 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 (83percent yield) of a solid judged to be pure by nmr and by tic.
99.6 %Spectr.
With potassium hydroxide; tetrabutyl phosphonium bromide In water; 4-methyl-2-pentanone at 115 - 120℃; for 5 h;
Example 3; n-Hexadecyl-3-amino-4-chlorobenzoate: A mixture of 32.7 g (0.264 moles) 45percent potassium hydroxide solution, 43 g (0.25moles) of 3-amino-4-chlorobenzoic acid, 200 g of methyl isobutyl ketone, 80.6g (0.264 moles) of 1-bromohexadecane and 4.4 g of tetrabutylphosphonium bromide (5 mole percent) were heated to reflux and water was removed by means of a Dean Stark trap. After 5 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 93.4 g (95percent yield) of a solid whose nmr weight percent assay was 99.6percent.
Preparation 1 3-Hexadecyloxy-2-methylenepropan-1-ol 1-Bromohexadecane (61.1 g), diethylformamide (200 ml) and 2-methylenepropane-1,3-diol (17.7 g) were mixed. Sodium hydride dispersion (55-60percent in oil, 21.8 g) was added over 10 minutes, and the mixture was then stirred at 55°C for 1 hour. The reaction mixture was cooled to room temperature and carefully quenched with water (400 ml), extracted with ether (2 * 200 ml), and the ether extracts were washed with water (200 ml), dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo . The product was purified through a column of silica gel 60 (70-230 mesh, 30 g) eluding with ether/pentane 1: 3. Further purification was achieved by chromatography on Waters PrepLC.(R)./System 500A using a prepPAK.(R).-500/SILICA cartridge with ether/pentane 1: 4 followed by ether as eluent. Mp. 38-40°C. Elemental analysis: calculated C 76.86percent, H 12.90percent, found C 76.82percent, H 12.85percent.
5-bromoisophthalic acid dihexadecane ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Add 3g to 50mL DMF solvent <strong>[23351-91-9]5-bromoisophthalic acid</strong> (0.012 mol) and 4.8 g potassium hydrogencarbonate (0.048 mol),Stir at room temperature to form a potassium salt.9.16g of n-bromohexadecane (0.03mol) was added to the mixed solution,The reaction was stirred at 90 C for 12 hours. Stop the reaction and allow the solution to cool to room temperature.It was poured into 300 mL of water and extracted with ethyl acetate.Dry over anhydrous sodium sulfate, filter and then dry the solvent.Column chromatography with petroleum ether/ethyl acetate (15/1) as eluentIsolation gave a white solid.
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