Dimethylformamide → 4-Formylbenzoyl chloride

HRID 747649Notes

Reaction equation

HRID 747649 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)(O)=[O:2].CN(C=O)C.C(Cl)(=O)C([Cl:20])=O>C(Cl)(Cl)Cl.C(Cl)Cl>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([Cl:20])=[O:2])=[CH:5][CH:6]=1)=[O:9]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 120884-Formylbenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 124246204-Formylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-carboxybenzaldehyde (4.50 g, 30 mmol) in CHCl3 (6 mL) and DCM (5 mL), containing a catalytic amount of DMF, was added oxalyl chloride (7.7 mL, 90 mmol). The mixture was stirred at 50° C. for 3 hours. The reaction was concentrated in vacuo and the residue was dried.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was dried

Sources & evidence

ORD record
ord-93132a4a67a041d6b20d7ac9739df54f
Source dataset
uspto-grants-2008_07
Patent number
US07396936B1

Reaction notes

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