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

Temperature

40 °C

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)−.

1. concentrationwas concentrated under reduced pressure
2. additionThe residue was diluted with EtOAc (50 mL)
3. washwashed with brine
4. customThe organic layer was separated
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in aqueous HCl (6N, 50 mL)
9. temperatureheated to reflux
10. temperatureAfter about 3 days the reaction mixture was cooled to room temperature
11. concentrationconcentrated under reduced pressure

ORD record

ord-e122ff7ed0ec4f6a95744a1a8b88209b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962629B2