Sodium Hydroxide → (2-Chloro-4-trifluoromethylphenyl)propynoic acid

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Reaction Steps

0.65 g (1.175 mmol) of ethyl (2-chloro-4-trifluoromethylphenyl)propynoate is dissolved in 20 mL of ethanol, combined with 2 mL of 2M sodium hydroxide solution, and stirred for 3 hours at ambient temperature. The reaction mixture is evaporated down, the residue is taken up in water, and extracted with ethyl acetate. The aqueous phase is combined with 2 mL of 1M hydrochloric acid and stirred for 1 hour at ambient temperature. Then it is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate. Yield: 0.14 g (48% of theory); C10H4ClF3O2 (M=248.59); calc.: molecular ion peak (M−H)−: 247/249; found: molecular ion peak (M−H)−: 247/249; Rf value: 0.09 (silica gel, petroleum ether/ethyl acetate (4:1)).

Provenance & Evidence