Lithium hydroxide, monohydrate → 4-Oxo-1-phenylcyclohexane-1-carboxylic acid

Participants

Reaction Steps

Lithium hydroxide monohydrate (11.08 g, 264 mmol) was added to a suspension of dimethyl 4-oxo-1-phenyl-1,3-cyclohexanedicarboxylate (Description 16, 25.5 g, 87.9 mmol) in methanol (250 mL), water (83 mL) and tetrahydrofuran (83 mL) and the mixture was heated under reflux for 3 days. The mixture was cooled and the tetrahydrofuran and methanol were evaporated under reduced pressure. The pH was adjusted to 1 with hydrochloric acid (5M) and the mixture was extracted with dichloromethane. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a light yellow solid (19 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.50–7.29 (5H, m), 2.29–2.73 (2H, m), 2.62–2.55 (2H, m), 2.47–2.41 (2H, m), and 2.35–2.27 (2H, m).

Provenance & Evidence