Dichloromethane → 4-Cyano-2,2-dimethylbutanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 4,4-dimethyl-5-oxopentanenitrile (1.0 g, 7.98 mmol) in t-BuOH (2 mL) was cooled to 0° C. and 5% aqueous NaH2PO4 solution (11 mL) was added dropwise. 1M KMnO4 solution (16 mL) was added dropwise to the reaction mixture at 0° C. followed by few drops of CH2Cl2 (0.5 mL). The reaction mixture was allowed to stir at 0° C. for 1 h, and quenched with sodium sulfite. 1.5N HCl was then added to adjust the pH of the solution to ˜3. The organic product was extracted with EtOAc and dried over anhydrous sodium sulfate. Solvent was removed under reduced pressure to get 4-cyano-2,2-dimethylbutanoic acid (0.9 g, crude), which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 5.55 (br s, 1H), 2.43-2.37 (m, 2H), 1.99-1.94 (m, 2H), 1.28-1.27 (m, 6H).

Provenance & Evidence