Oxalyl chloride → 2-Methoxy-4-nitrobenzoyl chloride

HRID 329375Notes

Reaction equation

HRID 329375 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].O.[CH3:8][O:9][C:10]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15]C=1C(O)=O>C(Cl)Cl.CN(C)C=O>[CH3:8][O:9][C:10]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 70350705HCID 70350705, compound

Product 1

HCID 30161132-Methoxy-4-nitrobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.81 ml) in methylene chloride (10 ml) was added dropwise to a solution of 2-methoxy-4-nitrobenzoic acid monohydrate (1 g) in methylene chloride (40 ml) and dimethylformamide (1 drop) and the reaction mixture was stirred at room temperature for 1 hour after gas evolution ceased. The solvent was then evaporated in vacuo to give an oil which was crystallised from cold ethyl acetate/hexane to give the title compound, yield 0.7 g.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customto give an oil which
  3. customwas crystallised from cold ethyl acetate/hexane

Sources & evidence

ORD record
ord-51d760f2c99540f98bd7a398640032ba
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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