Chloride → (9Z,12Z,15Z)-9,12,15-Octadecatrienoyl chloride

HRID 246822

Reaction equation

HRID 246822 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH3:18].C(Cl)(=O)C([Cl:24])=O.[Cl-]>C(Cl)(Cl)Cl>[C:1]([Cl:24])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 312ChlorideHCID 65578Oxalyl chlorideHCID 5280934Linolenic Acid

Product 1

HCID 6436844(9Z,12Z,15Z)-9,12,15-Octadecatrienoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 10 g of α-linolenic acid in 100 ml of anhydrous chloroform was kept cooled with ice and 4.6 g of oxalic chloride was added dropwise thereto. The solution containing the chloride was stirred at room temperature for three hours. The resultant reaction solution was dried under a vacuum. The α-linolenic acid chloride consequently formed was dissolved in 100 ml of anhydrous chloroform. The solution consequently obtained was cooled to -50° C. and 2.2 g of paraformaldenyde was added thereto and subsequently 12.2 g of zinc chloride was added thereto. Thereafter, the resultant reaction solution was stirred at room temperature for three hours. It was subjected to alumina chromatography. From the methylene chloride eluate consequently separated, 4.1 g of α-linolenyl oxymethyl chloride was obtained. The physicochemical data obtained of this product were as shown below. They prove the identity of α-linolenyl oxymethyl chloride.

Workup

  1. additionwas added dropwise
  2. customThe resultant reaction solution
  3. customwas dried under a vacuum

Sources & evidence

ORD record
ord-c8d454e56513413dbf3391f5977b4320
Source dataset
uspto-grants-1987_11
Patent number
US04704393

Linked notes

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