Dichloromethane → 4-Cyano-2,2-dimethylbutanoic acid
Reaction equation
[CH3:1][C:2]([CH3:9])([CH:7]=[O:8])[CH2:3][CH2:4][C:5]#[N:6].[O-:10][Mn](=O)(=O)=O.[K+].C(Cl)Cl>CC(O)(C)C>[C:5]([CH2:4][CH2:3][C:2]([CH3:9])([CH3:1])[C:7]([OH:10])=[O:8])#[N:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- customquenched with sodium sulfite
- addition1.5N HCl was then added
- extractionThe organic product was extracted with EtOAc
- dry with materialdried over anhydrous sodium sulfate
- customSolvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-7c86372f4f9b4410bc6bf350bf4a15fb
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08981084B2
Reaction notes
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