3-Methyl-2-nitrobenzoic acid → 3-methyl-2-nitrobenzoyl chloride

HRID 1263170Notes

Reaction equation

HRID 1263170 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:16])=O>>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([Cl:16])=[O:6])[C:3]=1[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 215753-Methyl-2-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 2671613-methyl-2-nitrobenzoyl chlorideYield 101.7%

Procedure

In this example 2.14 moles of 3-methyl-2-nitrobenzoic acid were refluxed with 6.43 moles (468 ml) of thionyl chloride for three hours and then allowed to stand overnight. The mixture was then again refluxed until the mixture turned a dark brown color. Excess thionyl chloride was removed by evaporation affording 434.4 g of the title product.

Workup

  1. temperatureThe mixture was then again refluxed until the mixture
  2. customExcess thionyl chloride was removed by evaporation

Sources & evidence

ORD record
ord-06193523d1fc49a8a8cecd24b8761887
Source dataset
uspto-grants-1984_06
Patent number
US04456471

Reaction notes

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