Reaktion #93915

Reaktionsgleichung

methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate

sodium chloride

dimethylsulfoxide

hydrochloric acid

→

title compound

Ausbeute 110.4%

8-methylsulfonyl-12-hydroxyheptadecanoic acid

Ausbeute 110.4%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated in a bath
2. 2
   SonstigeThe resulting reaction mixture
3. 3
   Einengenis concentrated in vacuo at 100° C.
4. 4
   Sonstigeproviding an oily residue which
5. 5
   Extraktionextracted with ether
6. 6
   ExtraktionThe organic extract
7. 7
   Waschenis washed with water
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated in vacuo

Vorschrift

A mixture of methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate (36.7 g., 0.077 mole), sodium chloride (4.68 g., 0.08 mole), water (1 ml.) and dimethylsulfoxide (60 ml.) is heated in a bath maintained at 185° C. under nitrogen for 5 hours. The resulting reaction mixture is concentrated in vacuo at 100° C. providing an oily residue which is diluted with water. The aqueous mixture is acidified to Congo Red with 6N hydrochloric acid and extracted with ether. The organic extract is washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo leaving the title compound as a viscous oil (31 g., 95%), pmr (CDCl3) δ 2.0 (s, 3H), 2.82 (s, 3H), 3.63 (s, 3H) and 4.9 (b, H).

Quelle