Reacción #52054

Ecuación de reacción

ethylacetate

Ethyl 2-ethoxy-6-pentadecyl-benzoate

lithium aluminum hydride

HCl

lithium aluminium hydride

→

2-ethoxy-6-pentadecyl-benzyl alcohol

Disolventes

hexane EtOAc

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Secadoto dry 250 mL three neck round bottom flask
2. 2
   Otrofitted
3. 3
   Temperaturawith reflux condenser, mechanical stirrer
4. 4
   Temperaturait was maintained under nitrogen atmosphere through out the reaction
5. 5
   OtroReaction
6. 6
   workup.ADDITIONAfter addition the solution
7. 7
   Temperaturamaintained at that temperature for about two hours
8. 8
   Otroorganic layer was separated
9. 9
   Secadodried over anhydrous sodium sulphate
10. 10
    Concentraciónconcentrated under vacuum
11. 11
    Otroto give a light brownish solid
12. 12
    OtroThis was recrystallised from petroleum ether (40-60° C.)
13. 13
    Otroto give white solid

Procedimiento

Ethyl 2-ethoxy-6-pentadecyl-benzoate (10.9 g, 27 mmol) was dissolved in dry tetrahydrofuran (60 mL). This solution was transferred to dry 250 mL three neck round bottom flask fitted with reflux condenser, mechanical stirrer and it was maintained under nitrogen atmosphere through out the reaction. To this lithium aluminum hydride (2.04 g, 54 mmol) was added slowly. Reaction was highly exothermic. After addition the solution was slowly brought to the reflux temperature and maintained at that temperature for about two hours and TLC was checked in hexane:EtOAc (8:2). After completion of reaction, excess lithium aluminium hydride was decomposed by drop-wise addition of ethylacetate (80 mL). To this 5 M HCl (100 mL) was added and organic layer was separated, dried over anhydrous sodium sulphate, concentrated under vacuum to give a light brownish solid. This was recrystallised from petroleum ether (40-60° C.) to give white solid. Yield: 8 g.

Fuente