5-Methyl-2-nitrobenzoic acid → 5-Methyl-2-nitrobenzoyl chloride

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:16])=O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([Cl:16])=[O:8]

Participants

Reactant 2

HCID 183715-Methyl-2-nitrobenzoic acid

HCID 24386Thionyl Chloride

Product 1

HCID 30160135-Methyl-2-nitrobenzoyl chloride

Procedure

A mixture of 5-methyl-2-nitrobenzoic acid (3.6 g, 19.87 mmol) and thionyl chloride (18 mL) was stirred under reflux for 20 hours then concentrated under reduced pressure to give 5-methyl-2-nitrobenzoyl chloride (3.77 g) which was used without further purification.

Workup

temperatureunder reflux for 20 hours
concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record: ord-2380136c791e4cb694bce3db9ce279d8
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541407B2

Reaction notes

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