Hydrochloric Acid → Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate

HRID 1111613Notes

Reaction equation

HRID 1111613 reaction equation
[Cl:1][C:2]([Cl:8])=[CH:3][CH:4]=[C:5]([CH3:7])[CH3:6].[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].O.[Cl-].[Li+].Cl>O.C(OCC)(=O)C>[C:9]([C:11]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:4]([CH:3]=[C:2]([Cl:8])[Cl:1])[C:5]1([CH3:7])[CH3:6])#[N:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 1087461,3-Pentadiene, 1,1-dichloro-4-methyl-HCID 23681138Lithium chloride hydrate

Product 1

HCID 12898169Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylateYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

151 Parts of 1,1-dichloro-4-methylpenta-1,3-diene, 113 parts of ethyl cyanoacetate, 200 parts of cupric acetate monohydrate, 148 parts of cupric chloride, 62.6 parts of lithium chloride monohydrate and 900 parts of ethyl acetate are stirred in an atmosphere of nitrogen. The temperature is raised to 80° C. and maintained at 80°-81° C. for 5 hours. After cooling, the reaction mixture was stirred with 1180 parts of hydrochloric acid (s.g. 1.18) and 1500 parts of water for 10 minutes. The organic layer was separated and extracted twice with 590 parts of hydrochloric acid (s.g. 1.18) in 500 parts of water. The ethyl acetate solution was diluted with 900 parts of ethyl acetate and the solution washed four times with 500 parts of water. The ethyl acetate solution is evaporated by heating to 87° C. at 20 mm Hg pressure to yield 201 parts of ethyl 1-cyano- 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate (estimated strength 82.7% equivalent to 63.4% yield).

Workup

  1. temperaturemaintained at 80°-81° C. for 5 hours
  2. temperatureAfter cooling
  3. customThe organic layer was separated
  4. extractionextracted twice with 590 parts of hydrochloric acid (s.g. 1.18) in 500 parts of water
  5. additionThe ethyl acetate solution was diluted with 900 parts of ethyl acetate
  6. washthe solution washed four times with 500 parts of water
  7. customThe ethyl acetate solution is evaporated
  8. temperatureby heating to 87° C. at 20 mm Hg pressure

Sources & evidence

ORD record
ord-118a6bd732654c07ada3bae25230823c
Source dataset
uspto-grants-1978_10
Patent number
US04118412

Reaction notes

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