Acetic Acid → 2,2-Dimethyl-4-oxocyclopentane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,4-dimethylcyclopent-2-enone (2.0 g, 18 mmol) in EtOH (50 mL), water (7.5 mL) and AcOH (1.5 mL) was added potassium cyanide (2.36 g, 36.3 mmol). The reaction mixture was heated to about 40° C. and after about 15 h the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (50 mL) and washed with brine. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was dissolved in aqueous HCl (6N, 50 mL) and heated to reflux. After about 3 days the reaction mixture was cooled to room temperature and concentrated under reduced pressure to provide 2,2-dimethyl-4-oxocyclopentanecarboxylic acid (3.7 g, 90%, ˜70% purity by 1H NMR) that was carried on without additional purification: LC/MS (Table 2, Method a) Rt=1.30 min; MS m/z: 155 (M−H)−.

Provenance & Evidence