Reaction #56578

Reaction equation

z,z,z-octadeca-6,9,12-trienoic acid

1,3-dihydroxypropane

1,3-dicyclohexylcarbodiimide

→

1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Filtrationwas filtered
2. 2
   WashThe filtrate was washed with dilute hydrochloric acid, water and saturated sodium chloride solution
3. 3
   OtherThe solution was dried
4. 4
   Concentrationconcentrated
5. 5
   Otherpurified
6. 6
   Otherby dry column chromatography

Procedure

A solution of z,z,z-octadeca-6,9,12-trienoic acid (150 g) in methylene chloride (500 ml) was added dropwise to a mixture of 1,3-dihydroxypropane (205 g), 1,3-dicyclohexylcarbodiimide (130 g) and 4-(N,N-dimethylamino)pyridine (87 g) in methylene chloride (2500 ml) at room temperature under nitrogen. When tlc indicated that the reaction had gone to completion the reaction mixture was filtered. The filtrate was washed with dilute hydrochloric acid, water and saturated sodium chloride solution. The solution was dried, concentrated and purified by dry column chromatography to yield 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane as a pale yellow oil.

Source