Thionyl Chloride → HCID 20485215, compound

HRID 647552Notes

Reaction equation

HRID 647552 reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][CH2:4][CH:5]([CH:9]([CH3:11])[CH3:10])[C:6](O)=[O:7].S(Cl)([Cl:15])=O>C1C=CC=CC=1>[Cl:1][C:2]([Cl:12])=[CH:3][CH2:4][CH:5]([CH:9]([CH3:11])[CH3:10])[C:6]([Cl:15])=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 129596915,5-Dichloro-2-isopropyl-4-pentenoic acid

Product 1

HCID 20485215HCID 20485215, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 2.1 g of α-(3,3-dichloroallyl)isovaleric acid were added 3.0 g of thionyl chloride, as well as 10 g of benzene, and the mixture was refluxed for 5 hours. Then, the reaction mixture was distilled to remove the low-boiling fraction. By this procedure there was obtained α-(3,3-dichloroallyl)isovaleroyl chloride. This chloride was dissolved in 30 g of dry benzene, followed by the addition of 2.0 g of 3-phenoxybenzyl alcohol. Then, 2.0 g of pyridine were added added dropwise and the mixture was stirred at room temperature overnight. The reaction mixture was then diluted with diethyl ether, washed with dilute hydrochloric acid and water, dried over anhydrous magnesium sulfate and distilled to remove the low-boiling fraction. The residual viscous oil was purified by column chromatography to recover 3.1 g of 3-phenoxybenzyl α-(3,3-dichloroallyl)isovalerate (Compound [5]) having the following properties [yield: 79% based on α-(3,3-dichloroallyl)isovaleric acid].

Workup

  1. distillationThen, the reaction mixture was distilled
  2. customto remove the low-boiling fraction

Sources & evidence

ORD record
ord-bf5089c6756942aba0314cc4ba5f91b0
Source dataset
uspto-grants-1983_10
Patent number
US04409238

Reaction notes

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