Oxalyl chloride → 3,4-Bis(tetradecyloxy)benzoyl chloride

HRID 248011Notes

Reaction equation

HRID 248011 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:19](O)=[O:20])[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:43])=O>C(Cl)Cl.CN(C)C=O>[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:19]([Cl:43])=[O:20])[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 190162583,4-Bis(tetradecyloxy)benzoic acid

Product 1

HCID 190161213,4-Bis(tetradecyloxy)benzoyl chlorideYield 98.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 5.0 g of product from Example 104 in 80 ml of methylene chloride and 5 drops of dimethylformamide is added 1.74 g of oxalyl chloride. The reaction is stirred at room temperature for 2.5 days and concentrated in vacuo. The residue is dissolved in diethyl ether, passed through a pad of diatomaceous earth and concentrated in vacuo to give 5.1 g of the desired product as colorless crystals.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in diethyl ether
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fd6e789a7c043fb9efbacb31ae381ed
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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