Water → 2,2-Dimethyl-3-phenylcyclopropanecarbonitrile

HRID 2240846Notes

Reaction equation

HRID 2240846 reaction equation
[C:1]([C:3]1(C(O)=O)[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:4]1([CH3:13])[CH3:12])#[N:2].[Li+].[Cl-].C([O-])(O)=O.[Na+].O>CS(C)=O.[Cl-].[Na+].O>[CH3:12][C:4]1([CH3:13])[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:3]1[C:1]#[N:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 135886061-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylic Acid

Product 1

HCID 134298982,2-Dimethyl-3-phenylcyclopropanecarbonitrileYield 76%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid (13.6 g, 63 mmol) in DMSO (125 mL) was added LiCl (10.72 g, 252 mmol) followed by NaHCO3 (7.96 g, 94.5 mmol) and water (4.55 g, 252 mmol). Gas evolution was observed, and within 30 minutes enough solids were dissolved to allow the milky mixture to stir. The reaction mixture was stirred at 170° C. for 18 hours, then cooled and poured into a mixture of water and brine (7/1, 800 mL) and extracted with ethyl ether. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give 7.79 g (76% yield) of 2,2-dimethyl-3-phenyl-cyclopropanecarbonitrile (3/1, cis/trans mixture).

Workup

  1. dissolutionwithin 30 minutes enough solids were dissolved
  2. stirringThe reaction mixture was stirred at 170° C. for 18 hours
  3. temperaturecooled
  4. extractionextracted with ethyl ether
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a43ea3e5926b4203aa0f5050855d2aa3
Source dataset
uspto-grants-2010_05
Patent number
US07723391B2

Reaction notes

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