Chloroform → 3-Methyl-2-[4-((((3,5-dimethylphenyl)amino)carbonyl)methyl)phenoxy]butanoic acid

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Reaction Steps

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. 5.45 ml (60 mmol) of isobutyraldehyde and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirring continued 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% NaHCO3 solution. The aqueous layer on acidification yields the product 3-methyl-2-[4-((((3,5-dimethylphenyl)amino)carbonyl)methyl)phenoxy] butanoic acid (C21H25NO4) (yield 1 gm, 23.5%) mp (uncorrected) 96°-100° C.

Provenance & Evidence