Réaction #52054

Équation de réaction

ethylacetate

Ethyl 2-ethoxy-6-pentadecyl-benzoate

lithium aluminum hydride

HCl

lithium aluminium hydride

→

2-ethoxy-6-pentadecyl-benzyl alcohol

Solvants

hexane EtOAc

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Séchageto dry 250 mL three neck round bottom flask
2. 2
   Autrefitted
3. 3
   Températurewith reflux condenser, mechanical stirrer
4. 4
   Températureit was maintained under nitrogen atmosphere through out the reaction
5. 5
   AutreReaction
6. 6
   workup.ADDITIONAfter addition the solution
7. 7
   Températuremaintained at that temperature for about two hours
8. 8
   Autreorganic layer was separated
9. 9
   Séchagedried over anhydrous sodium sulphate
10. 10
    Concentrationconcentrated under vacuum
11. 11
    Autreto give a light brownish solid
12. 12
    AutreThis was recrystallised from petroleum ether (40-60° C.)
13. 13
    Autreto give white solid

Mode opératoire

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.

Source