Реакция #52054

Уравнение реакции

ethylacetate

Ethyl 2-ethoxy-6-pentadecyl-benzoate

lithium aluminum hydride

HCl

lithium aluminium hydride

→

2-ethoxy-6-pentadecyl-benzyl alcohol

Растворители

hexane EtOAc

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Сушкаto dry 250 mL three neck round bottom flask
2. 2
   Другоеfitted
3. 3
   Температураwith reflux condenser, mechanical stirrer
4. 4
   Температураit was maintained under nitrogen atmosphere through out the reaction
5. 5
   ДругоеReaction
6. 6
   workup.ADDITIONAfter addition the solution
7. 7
   Температураmaintained at that temperature for about two hours
8. 8
   Другоеorganic layer was separated
9. 9
   Сушкаdried over anhydrous sodium sulphate
10. 10
    Концентрированиеconcentrated under vacuum
11. 11
    Другоеto give a light brownish solid
12. 12
    ДругоеThis was recrystallised from petroleum ether (40-60° C.)
13. 13
    Другоеto give white solid

Методика

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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