Dichloromethane → [1,1'-Biphenyl]-2,2'-dicarbonyl dichloride

HRID 2255002

Reaction equation

HRID 2255002 reaction equation
[C:1]1([C:10]2C(=[CH:15][CH:16]=[CH:17][CH:18]=2)C(O)=O)[C:2](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:3](O)=[O:4].[C:19](Cl)(=O)[C:20]([Cl:22])=[O:21].C(Cl)[Cl:26]>CN(C)C=O>[C:1]1([C:10]2[C:19](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]([Cl:22])=[O:21])[C:2](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:3]([Cl:26])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10210Diphenic acidHCID 65578Oxalyl chloride

Product 1

HCID 15621100[1,1'-Biphenyl]-2,2'-dicarbonyl dichloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.2 g of diphenic acid (biphenyl-2,2'-dicarboxylic acid) were dissolved in 200 ml of methylene chloride and 1 ml of N,N-dimethylformamide, and 27.9 g of oxalylchloride were dropped in the resultant solution under stirring at room temperature over 30 minutes. After the dropping, the resultant solution was reacted at room temperature for one hour, and the reaction solution was thickened in aspirator vacuum. Methylene chloride and an excessive amount of oxalylchloride were removed from the thickened solution to obtain an oily matter of diphenic acid chloride.

Workup

  1. customMethylene chloride and an excessive amount of oxalylchloride were removed from the thickened solution

Sources & evidence

ORD record
ord-55c525c0fd864487b2fd9a21a75df23c
Source dataset
uspto-grants-1993_08
Patent number
US05238790

Linked notes

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