Hydrochloric Acid → 6-(Trifluoroacetamido)hexanoic Acid

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Reaction Steps

Ethyl trifluoroacetate (7.1 g, 50 mmole) is added with stirring to a suspension of 6-aminocaproic acid (I, 5.0 g, 40 mmole) in methanol (25 ml) and triethylamine (40 mmole) is added, with stirring. After stirring for 12 hours, by which time all the acid is in solution, the mixture is diluted with methylene chloride (100 ml) and made acidic (pH 1) with 1 N HCl. Saturated sodium chloride solution (90 ml) is then added and the lower layer is separated. The aqueous layer is extracted with methylene chloride (100 ml) and the two organic extracts are combined, dried over sodium sulfate and the solvents evaporated to afford 5.21 g of the desired acid II (Scheme I).

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