Thionyl Chloride → 3-(But-1-en-1-yl)-2,2-dimethylcyclopropane-1-carbonyl chloride

HRID 412327Notes

Reaction equation

HRID 412327 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:4]([CH:5]=[CH:6][CH2:7][CH3:8])[CH:3]1[C:9](O)=[O:10].S(Cl)([Cl:15])=O>CN(C)C=O.CCCCCC>[CH3:1][C:2]1([CH3:12])[CH:4]([CH:5]=[CH:6][CH2:7][CH3:8])[CH:3]1[C:9]([Cl:15])=[O:10]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 54109341HCID 54109341, compound

Product 1

HCID 573588463-(But-1-en-1-yl)-2,2-dimethylcyclopropane-1-carbonyl chlorideYield 86.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

Fifty grams (50 g) of 2,2-dimethyl-3-(1-butenyl)cyclopropanecarboxylic acid, 350 ml of hexane and 0.6 g of N,N-dimethylformamide were mixed together. At 50° C., 39 g of thionyl chloride was eye-dropped thereto over 30 minutes. Subsequently, the reaction mixture was stirred for 1 hour at 50° C. The reaction mixture was then concentrated under reduced pressure to provide 48 g of 2,2-dimethyl-3-(1-butenyl)cyclopropane carboxylic chloride.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a86e43b98e84eff978165eeeedff3c6
Source dataset
uspto-grants-2003_05
Patent number
US06562853B2

Reaction notes

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