Thionyl Chloride → 3-Pentylcyclobutanecarboxylic acid chloride

HRID 1078022Notes

Reaction equation

HRID 1078022 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([CH:10]1[CH2:13][CH:12]([C:14]([OH:16])=O)[CH2:11]1)[CH2:6][CH2:7][CH2:8][CH3:9]>C1C=CC=CC=1>[CH2:5]([CH:10]1[CH2:13][CH:12]([C:14]([Cl:3])=[O:16])[CH2:11]1)[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 47799Cyclobutanecarboxylic acid, 3-pentyl-

Product 1

HCID 153402213-Pentylcyclobutanecarboxylic acid chlorideYield 91.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A reaction vessel was charged with 140 g of thionyl chloride and 100 ml of benzene, and 100 g of 3-pentylcyclobutanecarboxylic acid was added dropwise under reflux with stirring. The resultant mixture was refluxed with stirring for 8 hours and the excess thionyl chloride was azeotropically distilled off with benzene and the residue was distilled under reduced pressure to obtain 101 g (yield 91%) of 3-pentylcyclobutanecarboxylic acid chloride.

Workup

  1. additionwas added dropwise
  2. temperatureunder reflux
  3. stirringwith stirring for 8 hours
  4. distillationthe excess thionyl chloride was azeotropically distilled off with benzene
  5. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-71457bf1bded4e23b0cfd3ec1725f6c1
Source dataset
uspto-grants-1996_08
Patent number
US05545747

Reaction notes

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