Reacción #55585

Ecuación de reacción

ethyl 9-oxodecanoate ethylene ketal

lithium aluminum hydride

→

yellow oil

Rendimiento 116.6%

9-Oxodecan-1-ol

Rendimiento 116.6%

Disolventes

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by the dropwise addition of 18 ml of ethyl acetate
2. 2
   workup.ADDITIONTo this mixture there was then sequentially added in dropwise fashion
3. 3
   workup.STIRRINGwith stirring
4. 4
   workup.STIRRINGThe mixture was stirred for about 2 to 3 hr
5. 5
   Filtraciónthe mixture was then filtered
6. 6
   LavadoThe filter pad was rinsed several times with ether
7. 7
   OtroThe combined filtrates were evaporated in vacuo
8. 8
   workup.DISSOLUTIONThe residue was dissolved in a mixture of 250 ml of 10% hydrochloric acid and 120 ml of methanol
9. 9
   workup.WAITleft
10. 10
    workup.WAITto stand at room temperature for about 4 hr
11. 11
    OtroThe solution was evaporated in vacuo
12. 12
    workup.DISSOLUTIONThis residue was dissolved in ether
13. 13
    Lavadothe resulting solution was washed with saturated aqueous sodium chloride
14. 14
    Secadodried over anhydrous magnesium sulfate
15. 15
    Otroevaporated in vacuo

Procedimiento

A solution of 95.4 g (370 mmol) of ethyl 9-oxodecanoate ethylene ketal (prepared in Example 22A-1) in 120 ml of ether was added dropwise to a stirred mixture of 10.5 g (277 mmol) of lithium aluminum hydride and 500 ml of ether under argon. The mixture was stirred for 18 hr and then quenched by the dropwise addition of 18 ml of ethyl acetate. To this mixture there was then sequentially added in dropwise fashion, with stirring, 10.5 ml of water, 10.5 ml of 15% aqueous sodium hydroxide and 31.1 ml of water. The mixture was stirred for about 2 to 3 hr and the mixture was then filtered. The filter pad was rinsed several times with ether. The combined filtrates were evaporated in vacuo. The residue was dissolved in a mixture of 250 ml of 10% hydrochloric acid and 120 ml of methanol and left to stand at room temperature for about 4 hr. The solution was evaporated in vacuo. This residue was dissolved in ether and the resulting solution was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to yield 74.3 g of a yellow oil. The product had the following physical characteristics:

Fuente