Toluene → HCID 178445659, compound

Participants

Reaction Steps

A 2-necked round bottom flask, which had been dried and cooled under argon, was charged with cis/trans-4-isobutyl-cyclohexanecarboxylic acid methyl ester (7:3) (0.5 g, 2.5 mmol), dry toluene (10 ml) and sodium methoxide (0.41 g, 7.6 mmol). The reaction mixture was heated at reflux for 96 h. After cooling to room temperature the mixture was diluted with tert-butyl methyl ether (100 ml) and washed with ice-cold aqueous hydrochloric acid solution (pH 1). The aqueous layer was extracted with one 50-ml portion of tert-butyl methyl ether. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a (15:85) cis/trans mixture. MS m/e: 183 ([M−H]−)

Provenance & Evidence