反応 #1538314

反応方程式

lithium aluminium hydride

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

sulphuric acid

water

→

z,z,z,-octadeca-6,9,12-trienol

収率 94.2%

溶媒

diethyl ether

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   温度a steady reflux
3. 3
   温度The mixture was heated
4. 4
   温度under reflux for 4 hours
5. 5
   温度After cooling to 0°-5° C.
6. 6
   温度still maintaining a blanket of nitrogen
7. 7
   その他The aqueous layer was separated
8. 8
   洗浄the organic layer was washed with water (1000 ml), saturated aqueous sodium bicarbonate (2×1000 ml) and water (2×500 ml)
9. 9
   乾燥The ether layer was dried (Na2SO4)
10. 10
    その他evaporated in vacuo
11. 11
    その他to give a yellow oil
12. 12
    workup.DISTILLATIONDistillation (148°-150° C./0.06 mmHg)

実験手順

To a suspension of lithium aluminium hydride (50 g) in diethyl ether (1400 ml) under nitrogen was added dropwise with stirring a solution of z,z,z-octadeca-6,9,12-trienoic acid (97%, 200 g) at such a rate that a steady reflux occurred. The mixture was heated under reflux for 4 hours. After cooling to 0°-5° C., water (200 ml) was added cautiously to break down the complex, still maintaining a blanket of nitrogen. To the resulting slurry was added a 10% aqueous solution of sulphuric acid (1500 ml) and a two phase solution occurred. The aqueous layer was separated and the organic layer was washed with water (1000 ml), saturated aqueous sodium bicarbonate (2×1000 ml) and water (2×500 ml). The ether layer was dried (Na2SO4) and evaporated in vacuo to give a yellow oil. Distillation (148°-150° C./0.06 mmHg) gave z,z,z,-octadeca-6,9,12-trienol (179 g, 94% ) as a colourless oil.

出典