Реакция #3089

Уравнение реакции

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide

NaOH

cyclohexanone

CHCl3

→

HCl

cyclohexanecarboxylic acid

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеTHF is removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue is dissolved in water
3. 3
   ЭкстракцияThe precipitated solid is extracted into ether
4. 4
   workup.ADDITIONtreated with 6% sodium bicarbonate solution

Методика

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.

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