Thionyl Chloride → 4-Methoxy-3-nitrobenzoyl chloride

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].S(Cl)([Cl:17])=O>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:17])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 666404-Methoxy-3-nitrobenzoic acid

Product 1

HCID 123754634-Methoxy-3-nitrobenzoyl chloride

Procedure

4-methoxy-3-nitrobenzoic acid (10.0 g, 0.051 mol), and thionyl chloride (25 g, 0.212 mol), were refluxed together for 24 h. The reaction mixture was cooled to RT and concentrated to dryness. The off-white solid was carried onto the next step.

Workup

concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-153dd7436cdd4bf28126e895d90e9318
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178557B2

Reaction notes

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