Oxalyl chloride → 3-Chloro-4-(tetradecyloxy)benzoyl chloride

HRID 247947Notes

Reaction equation

HRID 247947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:5](O)=[O:6].C(Cl)(=O)C([Cl:29])=O>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:5]([Cl:29])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 190162833-Chloro-4-(tetradecyloxy)benzoic acid

Product 1

HCID 190162883-Chloro-4-(tetradecyloxy)benzoyl chlorideYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

To a mixture of 50.0 g of product from Example 37 in 700 ml of chloroform and 10 drops of dimethylformamide is added, dropwise, 25.8 g of oxalyl chloride. The reaction is stirred at room temperature for 18 hours and concentrated in vacuo. The residue is dissolved in diethyl ether, filtered and concentrated in vacuo to give 51.1 g of the desired product as white crystals.

Workup

  1. additionis added
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in diethyl ether
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ed6b747c3314191ae9f93f9bd53f764
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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