4-Nitrobenzoic Acid → 4-Nitrobenzoyl chloride

HRID 400313Notes

Reaction equation

HRID 400313 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 a precipitate, which
  7. filtrationis then filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-162e26bc9b7841bfbac2c9821c07a847
Source dataset
uspto-grants-2014_06
Patent number
US08741048B2

Reaction notes

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