Hydrochloric Acid → 2,2-Dimethyl-3-ethoxycarbonyl-cyclopropane-1-carbonitrile

HRID 1155651Notes

Reaction equation

HRID 1155651 reaction equation
CC[O-].[Na+].[CH2:5]([O:7][C:8]([CH2:10][C:11]([CH3:17])([CH3:16])[CH:12](Br)[C:13]#[N:14])=[O:9])[CH3:6].O.Cl>C(O)C>[CH2:5]([O:7][C:8]([CH:10]1[C:11]([CH3:17])([CH3:16])[CH:12]1[C:13]#[N:14])=[O:9])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723922Sodium ethoxideHCID 54309071HCID 54309071, compound

Product 1

HCID 128503382,2-Dimethyl-3-ethoxycarbonyl-cyclopropane-1-carbonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

8.15 g (0.12 mol) of sodium ethylate in 30 ml of ethanol were added dropwise to a solution of 24.8 g (0.1 mol) of 3-bromo-3-cyano-2,2-dimethyl-propane-1-carboxylic acid ethyl ester in 50 ml of ethanol. The mixture was subsequently stirred at 50°-60° C. for 3 hours. 200 ml of water were then added and the reaction mixture was neutralized with HCl and extracted twice with 50 ml of methylene chloride each time. The combined methylene chloride extracts were washed twice with 50 ml of H2O each time, dried over Na2SO4 and then concentrated. The residue was fractionated. 11.5 (69% theory) of 2-cyano-3,3-dimethyl-cyclopropane-1-carboxylic acid ethyl ester were obtained in the form of a colorless oil of boiling point 68°-72° C./2 mm Hg.

Workup

  1. extractionextracted twice with 50 ml of methylene chloride each time
  2. washThe combined methylene chloride extracts were washed twice with 50 ml of H2O each time
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3067d036ed144ae7bd8808c313f29dfb
Source dataset
uspto-grants-1982_06
Patent number
US04332745

Reaction notes

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