4-Nitrobenzoic Acid → 4-Nitrobenzoyl chloride

HRID 1161608Notes

Reaction equation

HRID 1161608 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:15])=O>>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([Cl:15])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 85024-Nitrobenzoyl chlorideYield 100%

Procedure

A mixture of p-nitrobenzoic acid (500 g, 3.0 moles, 1 equiv) and thionyl chloride (600 mL, 8.2 moles, 2.73 equiv) was heated to reflux for 6-7 hours until a clear solution was obtained. Excess of thionyl chloride was removed by distillation followed by co-distillation with toluene (300 mL). The reaction mass was cooled to room temperature, and hexane (1.5 L) was added, forming a precipitate, which was then filtered and dried under vacuum, yielding 4-nitrobenzoyl chloride as a yellow solid (530 g, approximately 100% yield), which was used without any further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6-7 hours until a clear solution
  3. customwas obtained
  4. customExcess of thionyl chloride was removed by distillation
  5. additionhexane (1.5 L) was added
  6. customforming a precipitate, which
  7. filtrationwas then filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-152dbcb13bfb4c10b5e673821dee5928
Source dataset
uspto-grants-2010_10
Patent number
US07819962B2

Reaction notes

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