反应详情

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. Subsequently 5.889 gms (60 mmol) of cyclohexanone and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirred overnight at room temperature. THF is removed under vacuum and the residue is dissolved in water, followed by acidification with 35% HCl. The precipitated solid is extracted into ether and treated with 6% sodium bicarbonate solution. The aqueous layer on acidification with HCl yields the product 1-[4-(((3,5-dimethylphenyl)amino)carbonyl) methyl)phenoxy] cyclohexanecarboxylic acid (C23H27NO4) The product was purified by repeated extraction into ether and NaHCO3.

1. customTHF is removed under vacuum
2. dissolutionthe residue is dissolved in water
3. extractionThe precipitated solid is extracted into ether
4. additiontreated with 6% sodium bicarbonate solution