Reaction #2028898

Reaction equation

thionyl chloride

Toluene

trans-4-propylcyclohexanecarboxylic acid

→

trans-4-propylcyclohexanecarboxylic acid chloride

Yield 98.0%

Solvents

Pyridine

Conditions

Workup

1. 1
   workup.DISTILLATIONThe unreacted thionyl chloride and the toluene were distilled off at atmospheric pressure
2. 2
   workup.DISTILLATIONThe residue was distilled under reduced pressure (83° C., 3 mmHg)

Procedure

Toluene (1,000 ml) was added to trans-4-propylcyclohexanecarboxylic acid (1) (500.0 g) in a reaction vessel under an atmosphere of nitrogen, and the mixture was heated to 50° C. Pyridine (0.70 ml) and thionyl chloride (360.0 g) were then added, and the stirring was continued for 3 hours. The unreacted thionyl chloride and the toluene were distilled off at atmospheric pressure. The residue was distilled under reduced pressure (83° C., 3 mmHg) to give trans-4-propylcyclohexanecarboxylic acid chloride (2) (531.7 g) in 98% yield.

Source