Ethylene Glycol → 4-Oxo-1-phenylcyclohexane-1-carboxylic acid

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Reaction Steps

4-Cyano-4-phenylcyclohexanone (25 mmol) was refluxed for 2 h with p-toluenesulfonic acid (2.5 mmol) and ethyleneglycol (30 mmol) in toluene (150 mL) using a Dean-Stark trap. The reaction mixture was partitioned between Et2O and 2 M NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The resulting oil was refluxed with KOH (40%, 200 mL) in ethyleneglycol (120 mL) for 3 h. Conc. HCl was added and the mixture was allowed to cool. It was than extracted with Et2O, dried (Na2SO4) and evaporated affording 4.4 g (81%) of the desired compound; 1H NMR (CDCl3) δ 2.2-2.5 (m, 4H), 2.55 (m, 2H), 2.74 (m, 2H), 7.25-7.50 (m, 5H), 8.0 (br, 1H).

Provenance & Evidence