Hydrochloric Acid → Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester

HRID 1390420Notes

Reaction equation

HRID 1390420 reaction equation
[Cl:1][C:2]([Cl:15])=[CH:3][CH:4]([C:11](Cl)([CH3:13])[CH3:12])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].CC(C)([O-])C.[Na+].Cl>CN(C)C=O>[CH3:12][C:11]1([CH3:13])[CH:4]([CH:3]=[C:2]([Cl:15])[Cl:1])[CH:5]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12503855Ethyl 5,5-dichloro-3-(2-chloropropan-2-yl)pent-4-enoateHCID 23676156Sodium t-butoxide

Product 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 274 g (1 mole) ethyl 3-(2,2-dichlorovinyl)-4-chloro-4-methyl-pentanoate in 1.5 liter of dry dimethylformamide (DMF) was cooled to 0° C. A suspension of 101 g (1.05 mole) sodium t-butoxide in 1 liter dry DMF was added to the solution over a period of 2 hours. The reaction mixture was then neutralized with dry HCl. The DMF was distilled off under vacuum to give a 90% yield of ethyl 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropane carboxylate. B.p. 85°-95° C./0.2-0.3 mm Hg.

Workup

  1. additionwas added to the solution over a period of 2 hours
  2. distillationThe DMF was distilled off under vacuum

Sources & evidence

ORD record
ord-251dedeb06e64747b62572c61572db7e
Source dataset
uspto-grants-1979_02
Patent number
US04138584

Reaction notes

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