Hydrochloric Acid → 4-Hydroxy-1-trifluoromethyl-cyclohexanecarboxylic acid methoxy-methyl-amide

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Reaction Steps

18.0 g (71.1 mmol) of 4-Oxo-1-trifluoromethyl-cyclohexanecarboxylic acid methoxy-methyl-amide (68) were dissolved in 350 ml of anhydrous ethanol and 2.96 g (78.2 mmol) of NaBH4 were added portionwise at −70° C. The mixture was then stirred for 1 h at ambient temperature, followed by addition of 500 ml of water. Initially, the pH was then adjusted to pH=4-5 using a 10% aqueous HCl-solution to remove remaining NaBH4. Afterwards, the pH was adjusted to pH=8 using saturated aqueous NaHCO3-solution and the ethanol was evaporated. The residual solution was extracted three times using 300 ml of ethyl acetate each. Afterwards, the organic layer was washed using 300 ml of a saturated aqueous NaCl-solution, dried over MgSO4 and evaporated. Chromatography on silica gel using ethyl acetate/n-heptane yielded 6.00 g of 69 as a colourless oil, containing only one cis/trans isomer of unknown configuration. Rt=0.66 min (Method P).

Provenance & Evidence