Thionyl Chloride → HCID 86738247, compound

HRID 1155145Notes

Reaction equation

HRID 1155145 reaction equation
[CH3:1][C:2]1([CH3:13])[C@@H:4]([CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])[C@@H:3]1[C:10](O)=[O:11].S(Cl)([Cl:16])=O>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:13])[C@@H:4]([CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])[C@@H:3]1[C:10]([Cl:16])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22813596HCID 22813596, compound

Product 1

HCID 86738247HCID 86738247, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into 50 ml of water were dissolved 11.0 g of sodium hydroxide, followed by the addition of 50.0 g of ethyl cis, trans-2,2-dimethyl-3-(2,2,2-trichloroethyl) cyclopropanecarboxylate and about 100 ml of ethanol as a solvent. This mixture was stirred at room temperature for one day. To the reaction mixture was further added a solution of 8.0 g sodium hydroxide in 15 ml of water and the mixture was stirred at room temperature for two days. The resultant reaction mixture was distilled under reduced pressure to remove ethanol and extracted with diethyl ether to recover the unreacted ethyl cis, trans-2,2-dimethyl-3-(2,2,2-trichloroethyl) cyclopropanecarboxylate. Then, the alkaline aqueous layer was acidified by the addition of hydrochloric acid and extracted with diethyl ether. The ethereal layer was dried over anhydrous magnesium sulfate and distilled to remove diethyl ether. By the above procedure there were obtained 45.2 g of cis, trans-2,2-dimethyl-3-(2,2,2-trichloroethyl) cyclopropanecarboxylic acid. To 45.2 g of the carboxylic acid were added 131 g of thionyl chloride and 150 g of benzene and the mixture was heated under reflux overnight. The reaction mixture was then distilled under reduced pressure to remove the low-boiling fraction. The resultant residue was purified by distillation under reduced pressure to obtain 37.2 g of cis, trans-2,2-dimethyl-3-(2,2,2-trichloroethyl) cyclopropanecarboxylic acid chloride which displayed the following NMR spectrum [yield 77% based on the ethyl cis, trans-2,2-dimethyl-3-(2,2,2-trichloroethyl) cyclopropanecarboxylate].

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. distillationThe reaction mixture was then distilled under reduced pressure
  4. customto remove the low-boiling fraction
  5. distillationThe resultant residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-ad50b004fc544e1cae4c126dce295bf6
Source dataset
uspto-grants-1981_11
Patent number
US04299839

Reaction notes

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