4-Nitrobenzoic Acid → 4-Nitrobenzoyl chloride

HRID 2403043Notes

Reaction equation

HRID 2403043 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) is heated to reflux for approximately 6-7 hours until a clear solution is obtained. Excess of thionyl chloride is removed by distillation followed by co-distillation with toluene (300 mL). The reaction mass is cooled to room temperature, and hexane (1.5 L) is added, forming; a precipitate, which is then filtered and dried under vacuum, yielding 4-nitrobenzoyl chloride as a yellow solid (530 g, approximately 100% yield), which is used without any further purification.

Workup

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

Sources & evidence

ORD record
ord-7b2dd65437be41c68274652a7a7bd33c
Source dataset
uspto-grants-2014_08
Patent number
US08801166B2

Reaction notes

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