Oxalyl chloride → Benzoyl chloride, 4-(tetradecyloxy)-

HRID 483559

Reaction equation

HRID 483559 reaction equation
[CH2:1]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(Cl)(=O)C([Cl:28])=O>C(Cl)(Cl)Cl.CN(C)C=O>[CH2:1]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([Cl:28])=[O:21])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2894104-(Tetradecyloxy)benzoic acid

Product 1

HCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-Yield 102.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 50 g of p-(tetradecyloxy)benzoic acid and 28.46 g of oxalyl chloride in 500 ml of chloroform containing 10 drops of N,N-dimethylformamide is stirred for 18 hours at ambient temperature. The solvent is evaporated and the residue dissolved in ether, filtered and evaporated to give 54 g of the desired product as a white solid.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in ether
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1525193c99d5448682c4d78a085ff665
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Linked notes

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