Thionyl Chloride → 4-Decyloxybenzoyl chloride

HRID 1032869

Reaction equation

HRID 1032869 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>CN(C)C=O.C(Cl)(Cl)(Cl)Cl>[CH2:5]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([Cl:3])=[O:21])=[CH:18][CH:17]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 1385274-(Decyloxy)benzoic acid

Product 1

HCID 117793534-Decyloxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A 300 ml two-necked flask equipped with a stirrer and a reflux condenser was charged with 100 ml of carbon tetrachloride, 4.5 ml of thionyl chloride and 11.1 g of 4-n-decyloxybenzoic acid obtained by a conventional method, and heated under reflux together with one drop of dimethylformamide for 4 hours. Then, unreacted thionyl chloride was removed under reduced pressure to obtain 4-decyloxybenzoyl chloride as a colorless liquid.

Workup

  1. customA 300 ml two-necked flask equipped with a stirrer and a reflux condenser
  2. customobtained by a conventional method
  3. temperatureheated
  4. customThen, unreacted thionyl chloride was removed under reduced pressure

Sources & evidence

ORD record
ord-de8ea2b0bfca4db4a062d4e0f3d4eec8
Source dataset
uspto-grants-1994_05
Patent number
US05308536

Linked notes

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