Реакция #322882

Уравнение реакции

sodium hydride

sodium iodide

tetradecylbromide

ethyl p-hydroxybenzoate

→

desired title compound

Выход 53.0%

Ethyl 4-tetradecyloxybenzoate

Выход 53.0%

Растворители

water

dimethylformamide

dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe solid was collected
2. 2
   Промывкаwashed with water
3. 3
   workup.ADDITIONmixed with hot (about 50° C.) ethyl acetate
4. 4
   Промывкаwashed with water
5. 5
   Другоеdried
6. 6
   ДругоеThe solvent was removed
7. 7
   Другоеthe residue recrystallized from ethanol

Методика

To a stirred mixture of about 39.7 g of about 50% sodium hydride, about 13.5 g of sodium iodide and about 208.58 g of tetradecylbromide in about 750 ml of dimethylformamide at about 0° C. was added a solution of about 125 g of ethyl p-hydroxybenzoate in about 400 ml of dimethylformamide over about 1/2 hour. The mixture was stirred at room temperature for about 67 hours and then poured into about 2 liters of water. The solid was collected, washed with water, mixed with hot (about 50° C.) ethyl acetate, washed with water and dried. The solvent was removed and the residue recrystallized from ethanol, giving about 144.57 g of the desired title compound, mp 34°-35° C.

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