Nitromethane → (1-Nitromethylcyclohexyl)acetic acid ethyl ester

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Reaction Steps

14.8 g (0.088 mol) of the cyclohexylideneacetic acid ethyl ester produced according to 1.1 were dissolved in 50 ml of tetrahydrofuran, 7.11 ml (0.132 mol) of nitromethane and 88 ml of tetrabutylammonium fluoride (1 molar in tetrahydrofuran) were added under a nitrogen atmosphere and refluxed for 20 hours. After cooling, the mixture was diluted with 50 ml of water and extracted three times with dieethyl ether. The organic phase was washed with 10 wt. % aqueous potassium hydrogensulfate solution and then washed with water, dried over magnesium sulfate and evaporated. (1-Nitromethylcyclohexyl)acetic acid ethyl ester was obtained as an orange-yellow oily liquid. The yield amounted to 19.8 g (98% of theoretical).

Provenance & Evidence