Water → 2,2-Dimethyl-3-ethoxycarbonyl-cyclopropane-1-carbonitrile

HRID 1660096Notes

Reaction equation

HRID 1660096 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(C(OCC)=O)[C:8]([CH3:10])([CH3:9])[CH:7]1[C:11]#[N:12])=[O:5])[CH3:2].O.CN(C)C=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[C:8]([CH3:9])([CH3:10])[CH:7]1[C:11]#[N:12])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 13102273HCID 13102273, compound

Product 1

HCID 128503382,2-Dimethyl-3-ethoxycarbonyl-cyclopropane-1-carbonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 71.7 g (0.3 mol) of 3,3-dimethyl-2-cyano-cyclopropane-1,1-dicarboxylic acid diethyl ester, 6 ml of water and 100 ml of dimethylformamide was heated to the boiling point under reflux for 20 hours. For working up, the mixture was diluted with toluene, washed twice with 300 ml of water each time, dried and distilled. 30.6 g (61% of theory) of 3,3-dimethyl-2-cyano-cyclopropane-1-carboxylic acid ethyl ester of boiling point 87°-95° C./2 mbar were obtained.

Workup

  1. temperaturewas heated to the boiling point
  2. temperatureunder reflux for 20 hours
  3. washwashed twice with 300 ml of water each time
  4. customdried
  5. distillationdistilled

Sources & evidence

ORD record
ord-92e6e31387c64959ae9b6fd97bb610ef
Source dataset
uspto-grants-1981_12
Patent number
US04307033

Reaction notes

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