Thionyl Chloride → HCID 10869449, compound

HRID 1788329Notes

Reaction equation

HRID 1788329 reaction equation
S(Cl)([Cl:3])=O.[C:5]([OH:22])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O>[C:5]([Cl:3])(=[O:22])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride3×HCID 445638Palmitoleic Acid

Product 1

HCID 10869449HCID 10869449, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 13.15 ml (180 mmol) of thionyl chloride, and a water condenser, is placed 28.45 ml (100 mmol) of palmitoleic acid. Addition of the thionyl chloride is completed with heating to about 40° C. over the course of about 30 minutes. When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 55 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, (Z)-hexadec-9-enoyl chloride. This acyl chloride, 10.95 g (40 mmol), is put into a dry separatory funnel and combined with 75 ml of dry dichloromethane for use in the next step of the reaction.

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-f633fdfc486c446da53f2012bb61b1c9
Source dataset
uspto-grants-2009_03
Patent number
US07511163B2

Reaction notes

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