Toluene → HCID 178448094, compound

HRID 1941716Notes

Reaction equation

HRID 1941716 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)[CH2:9][CH3:10].S(Cl)([Cl:22])=O>N1C=CC=CC=1>[CH2:8]([C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([Cl:22])=[O:19])[CH2:13][CH2:12]1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 178448101HCID 178448101, compound

Product 1

HCID 178448094HCID 178448094, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

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.

Workup

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

Sources & evidence

ORD record
ord-f105b3a34ccc416292640079d722cd07
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

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