Thionyl Chloride → 3-methoxy-4-nitro-benzoyl Chloride

HRID 2234459Notes

Reaction equation

HRID 2234459 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](O)=[O:7].S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([Cl:17])=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 111276553-methoxy-4-nitro-benzoyl ChlorideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-methoxy-4-nitrobenzoic acid (Aldrich; 9 g, 45.65 mmol) was suspended in toluene (90 mL) and thionyl chloride (9.99 mL, 136.95 mmol) added and the mixture heated to reflux for 1 hour. The reaction was evaporated to yield the title compound as a brown solid (9.84 g, 100%).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1 hour
  3. customThe reaction was evaporated

Sources & evidence

ORD record
ord-7221e81745f94a05855b8465ae127515
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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