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

HRID 1728790Notes

Reaction equation

HRID 1728790 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>CN(C)C=O.C(Cl)Cl>[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)-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a room temperature suspension of 15 g of product from Example 2, 160 ml methylene chloride and 5 drops dimethylformamide is added 5.87 ml oxalyl chloride. The reaction mixture is stirred at room temperature for 18 hours, concentrated in vacuo, dissolved in 300 ml of diethyl ether, filtered through diatomaceous earth and the filtrate concentrated in vacuo to give 15.5 g of the desired product.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in 300 ml of diethyl ether
  3. filtrationfiltered through diatomaceous earth
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-dddfe8eae3ad4bc69c3f51f274585e17
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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