Reaktion #52054

Reaktionsgleichung

ethylacetate

Ethyl 2-ethoxy-6-pentadecyl-benzoate

lithium aluminum hydride

HCl

lithium aluminium hydride

→

2-ethoxy-6-pentadecyl-benzyl alcohol

Lösungsmittel

hexane EtOAc

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Trocknento dry 250 mL three neck round bottom flask
2. 2
   Sonstigefitted
3. 3
   Temperaturwith reflux condenser, mechanical stirrer
4. 4
   Temperaturit was maintained under nitrogen atmosphere through out the reaction
5. 5
   SonstigeReaction
6. 6
   workup.ADDITIONAfter addition the solution
7. 7
   Temperaturmaintained at that temperature for about two hours
8. 8
   Sonstigeorganic layer was separated
9. 9
   Trocknendried over anhydrous sodium sulphate
10. 10
    Einengenconcentrated under vacuum
11. 11
    Sonstigeto give a light brownish solid
12. 12
    SonstigeThis was recrystallised from petroleum ether (40-60° C.)
13. 13
    Sonstigeto give white solid

Vorschrift

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.

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