Stearic Acid → Stearoyl chloride

HRID 1762409Notes

Reaction equation

HRID 1762409 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)(=O)C([Cl:24])=O>C(Cl)CCl>[C:1]([Cl:24])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 5281Stearic AcidHCID 65578Oxalyl chloride

Product 1

HCID 8212Stearoyl chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

1420g (5 moles) of stearic acid and 6 liters of ethylene dichloride are placed in a 12-liter flask and warmed to 45° C. 1270 g (10 moles) of oxalyl chloride is added dropwise over a 2.5 hour time period. After 1 hour of refluxing, the flask is blanketed with argon and cooled overnight. The solvent is removed and the stearoyl chloride is used without further purification.

Workup

  1. temperatureAfter 1 hour of refluxing
  2. temperaturecooled overnight
  3. customThe solvent is removed
  4. customthe stearoyl chloride is used without further purification

Sources & evidence

ORD record
ord-1bb8f69e802540dabd0ffa6366128062
Source dataset
uspto-grants-1989_05
Patent number
US04832975

Reaction notes

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