3-Cyclohexene-1-carboxylic acid → 3-Cyclohexene-1-carbonyl chloride

HRID 431179Notes

Reaction equation

HRID 431179 reaction equation
[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.S(Cl)([Cl:12])=O>CN(C)C=O.C1(C)C=CC=CC=1>[CH:1]1([C:7]([Cl:12])=[O:9])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 2

HCID 209033-Cyclohexene-1-carboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 5230583-Cyclohexene-1-carbonyl chlorideYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

An acid chloride was prepared as follows: anhydrous 3-cyclohexenecarboxylic acid (50 g, 0.4 mol) was placed in a 500 mL round-bottom flask and a few drops of N,N-dimethylformamide was added as a catalyst. To this was added dropwise thionyl chloride (58.4 mL, 0.8 mol), diluted with anhydrous toluene (50 mL), at room temperature and the reaction mixture was refluxed for 4 hours. The final product was fractionally distilled to yield 48.8 grams of 3-cyclohexenecarboxylic acid chloride at a yield of 85%.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 hours
  2. distillationThe final product was fractionally distilled

Sources & evidence

ORD record
ord-462b2f5b912240f4854761d9d08bc1ae
Source dataset
uspto-grants-2003_12
Patent number
US06657031B1

Reaction notes

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