Stearic Acid → Stearoyl chloride

HRID 1788316Notes

Reaction equation

HRID 1788316 reaction equation
S(Cl)([Cl:3])=O.[C:5]([OH:24])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O>[C:5]([Cl:3])(=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 5281Stearic AcidHCID 24386Thionyl Chloride3×

Product 1

HCID 8212Stearoyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 4.81 ml (66 mmol) of thionyl chloride, and a water condenser, is placed 15.65 g (55 mmol) of stearic acid. Addition of the thionyl chloride is completed with heating to about 45° C. over the course of about 40 minutes. When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 45 minutes. The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled. The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl chloride, stearoyl chloride.

Workup

  1. customIn a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer
  2. customfixed with a separatory funnel
  3. temperatureis heated
  4. distillationthe crude mixture is distilled
  5. distillationThe crude distillate in the receiving flask is then fractionally distilled

Sources & evidence

ORD record
ord-e51685ad3b0e4bb78719ec30d7f5f84a
Source dataset
uspto-grants-2009_03
Patent number
US07511164B2

Reaction notes

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