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

HRID 894490Notes

Reaction equation

HRID 894490 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[Cl:9][C:10]([Cl:16])=[CH:11][CH:12]=[C:13]([CH3:15])[CH3:14].O.[Cl-].[Li+].C([O-])(=O)C.[K+].ClCl>C(#N)C>[C:1]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:12]([CH:11]=[C:10]([Cl:16])[Cl:9])[C:13]1([CH3:15])[CH3:14])#[N:2]

Participants

7

Reactant 5

HCID 7764Ethyl cyanoacetateHCID 24526ChlorineHCID 1087461,3-Pentadiene, 1,1-dichloro-4-methyl-HCID 517044Potassium AcetateHCID 23681138Lithium chloride hydrate

Product 1

HCID 12898169Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of ethyl cyanoacetate (12.44 parts), 1,1-dichloro-4-methylpenta-1,3diene (15.1 parts), lithium chloride monohydrate (6.26 parts), cupric acetate monohydrate, and in one case potassium acetate, as indicated in the table below, in acetonitrile (100 parts by volume), is heated and chlorine is added at a uniform rate, heating being continued for a further period. After cooling the reaction mixture the acetonitrile is removed by distillation under reduced pressure and the ethyl 1-cyano-3-(2',2'-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate is isolated as described for Examples 41 to 48. The yield, strength and composition of the product, together with other preparative details, are given in the table below.

Workup

  1. temperatureis heated
  2. temperatureheating
  3. waitbeing continued for a further period
  4. customis removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1113741844ac4206b377386a69aabc93
Source dataset
uspto-grants-1981_08
Patent number
US04284582

Reaction notes

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