Reaktion #2028898

ord-f105b3a34ccc416292640079d722cd07

Reaktionsgleichung

O=S(Cl)Cl
thionyl chloride
Cc1ccccc1
Toluene
CCC[C@H]1CC[C@H](C(=O)O)CC1
trans-4-propylcyclohexanecarboxylic acid
CCC[C@H]1CC[C@H](C(=O)Cl)CC1
trans-4-propylcyclohexanecarboxylic acid chloride
Ausbeute 98.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  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)

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08389073B2uspto-grants-2013_03