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

HRID 248014Notes

Reaction equation

HRID 248014 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:12](O)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:12]([Cl:29])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 190152233,4-Bis(heptyloxy)benzoic acid

Product 1

HCID 190151863,4-Bis(heptyloxy)benzoyl chlorideYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a room temperature mixture of 5 g of product from Example 110 in 80 ml of methylene chloride and 5 drops of dimethylformamide is added 2.72 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 5.27 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-f40450762ba04fa091ae32076310a223
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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