4-Nitrobenzoic Acid → 4-Nitrobenzoyl chloride

HRID 1665632Notes

Reaction equation

HRID 1665632 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[N+:7]([C:10]1[CH:18]=[CH:17]C(C(O)=O)=[CH:12][CH:11]=1)([O-:9])=[O:8]>C(Cl)(Cl)Cl.CN(C=O)C>[N+:7]([C:10]1[CH:18]=[CH:17][C:1]([C:2]([Cl:4])=[O:3])=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 65578Oxalyl chloride

Product 1

HCID 85024-Nitrobenzoyl chlorideYield 101.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

Oxalyl chloride (4.78 g, 37.6 mmol) was added drop wise to a stirred solution of 4-nitrobenzoic acid (4.2 g, 25 mmol) in chloroform (50 mL). After 5 mins DMF (2 drops) was added and the resulting mixture was stirred at room temperature for 2 hours. The solvent was removed to afford 4.7 g (98%) of 4-nitro-benzoyl chloride which was used for next step without further purification.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-2f3e61b8005b434fb759d911b4da460f
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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