Reaktion #93919

Reaktionsgleichung

ethyl 8-(2-chloroethylsulfonyl)-12-acetoxyheptadecanoate

sodium hydroxide

water

→

title compound

8-vinylsulfonyl-12-hydroxyheptadecanoic acid

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeMost of the tetrahydrofuran is removed by evaporation in vacuo
2. 2
   Sonstigeat 30° C. or below
3. 3
   workup.ADDITIONThe residue is diluted with water (300 ml.)
4. 4
   Extraktionextracted with ether
5. 5
   Waschenwashed with water
6. 6
   Trocknendried over sodium sulfate
7. 7
   SonstigeThe ether is evaporated
8. 8
   Sonstigeto leave the product as a yellowish, very viscous oil
9. 9
   SonstigePurification
10. 10
    Waschenas eluting solvent mixture

Vorschrift

A mixture of ethyl 8-(2-chloroethylsulfonyl)-12-acetoxyheptadecanoate (43.5 g., 0.09 mole), sodium hydroxide (14.4 g., 0.36 mole), water (150 ml.) and tetrahydrofuran (600 ml.) is stirred at 25° C. for 24 hours. Most of the tetrahydrofuran is removed by evaporation in vacuo keeping the temperature of the evaporating solution at 30° C. or below. The residue is diluted with water (300 ml.) and extracted with ether. The aqueous solution is acidified with dilute hydrochloric acid. The oily product is taken up in ether, washed with water and dried over sodium sulfate. The ether is evaporated to leave the product as a yellowish, very viscous oil. Purification is effected by column chromatography on silica gel with benzene-dioxane as eluting solvent mixture. The title compound is obtained as a colorless viscous oil.

Quelle