Реакция #1376579

Уравнение реакции

12-bromododecanol

tetrahydrofuran

benzyl bromide

tetrahydrofuran

sodium hydride

tetrahydrofuran

→

1-bromo-12-benzyloxydodecane

Выход 65.7%

Растворители

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added to the reaction mixture
2. 2
   ДругоеThe resultant reaction mixture
3. 3
   Температураunder reflux for 2.5 hours
4. 4
   Экстракцияan organic layer was extracted with toluene
5. 5
   ПромывкаThe toluene layer was washed with water
6. 6
   Сушкаdried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThereafter, the solvent was distilled away
8. 8
   ДругоеThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/3)

Методика

First, 2.4 g of 60% sodium hydride and 100 ml of dry tetrahydrofuran were placed in a 300 ml flask whose content was replaced with argon. Then, 15 ml of a tetrahydrofuran solution containing 11.3 g of benzyl bromide, 15 ml of a tetrahydrofuran solution containing 15.9 g of 12-bromododecanol, and 0.1 g of tetrabutylammonium iodide were added to the reaction mixture. The resultant reaction mixture was stirred under reflux for 2.5 hours. The reaction mixture was poured into water, and an organic layer was extracted with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/3) to obtain 14.0 g of 1-bromo-12-benzyloxydodecane (Y: 65.7%). The compound thus obtained had a purity of 98.4% by GC.

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