Trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid → trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chloride

HRID 1156081Notes

Reaction equation

HRID 1156081 reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][C@H:4]1[C@H:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].C(Cl)(=O)C([Cl:16])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]([Cl:12])=[CH:3][C@H:4]1[C@H:6]([C:7]([Cl:16])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 41539Trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acidHCID 65578Oxalyl chloride

Product 1

HCID 11009700trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chlorideYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 13A, the reaction of 25.0 g (0.12 mole) of (±)-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid, 180 ml of toluene, and 30.4 g (0.24 mole) of oxalyl chloride gave 25.8 g of (±)-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride. The nmr spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-dda877b1bcd14232addd42ae9acae351
Source dataset
uspto-grants-1982_06
Patent number
US04333950

Reaction notes

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