Ethanol → HCID 53671598, compound

Participants

Reaction Steps

64.64 grams (g) (0.198 mole) of N-crotyl-m-trifluoromethyl dichloroacetanilide and 300 milliliters (mL) of absolute ethanol were added to a round-bottomed flask, and stirred at room temperature, followed by the addition of 14.39 g of potassium hydroxide in 20 mL of water dropwise over a period of 10 minutes. After the addition was complete, the reaction mixture solidified with the precipitation of potassium dichloroacetate. The flask was swirled by hand to break up the solidified cake and stirring allowed to continue for an additional 18 hours. At the end of this time, 250 mL of ethylacetate was added and the mixture filtered. The solvent was then removed in vacuo to yield a pale orange-yellow semisolid. This was partitioned between 300 mL of ethylacetate and 300 mL of water and the layers were separated. The organic layer was washed one time with 200 mL of water and one time with 200 mL of a saturated sodium chloride solution. The organic layer was then dried with sodium sulfate and the solvent removed in vacuo to yield a yellow-orange material that was distilled at aspirator pressure to yield 36.6 g (86%) of product, N-crotyl-m-trifluoromethyl aniline.

Provenance & Evidence