تفاعل #93919

معادلة التفاعل

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

sodium hydroxide

water

→

title compound

8-vinylsulfonyl-12-hydroxyheptadecanoic acid

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىMost of the tetrahydrofuran is removed by evaporation in vacuo
2. 2
   أخرىat 30° C. or below
3. 3
   workup.ADDITIONThe residue is diluted with water (300 ml.)
4. 4
   استخلاصextracted with ether
5. 5
   غسيلwashed with water
6. 6
   تجفيفdried over sodium sulfate
7. 7
   أخرىThe ether is evaporated
8. 8
   أخرىto leave the product as a yellowish, very viscous oil
9. 9
   أخرىPurification
10. 10
    غسيلas eluting solvent mixture

الإجراء التجريبي

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.

المصدر