Tridecanoic acid → Tridecanoyl chloride

HRID 848934Notes

Reaction equation

HRID 848934 reaction equation
[C:1]([OH:15])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].S(Cl)([Cl:18])=O>C1CCCCC1>[C:1]([Cl:18])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 12530Tridecanoic acid2×HCID 24386Thionyl Chloride2×

Product 1

HCID 87288Tridecanoyl chlorideYield 101.4%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
80 °C

Procedure

In a one L (liter) two-necked flask were placed 158.7 g (0.74 mol) of tridecanoic acid and 200 milliliter (mL) of cyclohexane, and the flask was equipped with a 100 mL dropping funnel containing 83.3 g (0.7 mol) of thionyl chloride and a reflux tube. Then, the tridecanoic acid was completely dissolved under heating and stirring of the flask in an oil bath at 80° C. Thereafter the thionyl chloride was added dropwise over a period of 2 hours, and further the oil bath was maintained at 80° C. for one hour. From the resultant reaction solution were removed the cyclohexane and the thionyl chloride under reduced pressure by means of an aspirator. The resultant reaction mixture was subjected to vacuum distillation. Thus 166.0 g (0.71 mol) of tridecanoyl chloride was obtained in a yield of 95.9% based on the fed tridecanoic acid.

Workup

  1. customthe flask was equipped with a 100 mL
  2. temperatureunder heating
  3. temperaturefurther the oil bath was maintained at 80° C. for one hour
  4. customFrom the resultant reaction solution
  5. customwere removed the cyclohexane
  6. customThe resultant reaction mixture
  7. distillationwas subjected to vacuum distillation

Sources & evidence

ORD record
ord-07b54417f7544887b05cd50df5c187a3
Source dataset
uspto-grants-2000_01
Patent number
US06010708

Reaction notes

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