Reaction #487495

Reaction equation

p-nitrobenzoic acid

thionyl chloride

→

4-nitrobenzoyl chloride

Yield 100.0%

Conditions

Workup

1. 1
   Temperatureis heated
2. 2
   Temperatureto reflux for approximately 6-7 hours until a clear solution
3. 3
   Otheris obtained
4. 4
   OtherExcess of thionyl chloride is removed by distillation
5. 5
   workup.ADDITIONhexane (1.5 L) is added
6. 6
   Otherforming a precipitate, which
7. 7
   Filtrationis then filtered
8. 8
   Otherdried under vacuum

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.

Source