Реакция #586117

Уравнение реакции

4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

sodium hydride

2-ethoxyethyl bromide

→

5,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

Выход 86.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe medium is stirred at room temperature for 2 hours
2. 2
   Экстракцияhydrolysed and extracted with ethyl ether
3. 3
   ПромывкаThe organic phase is washed with 1N sodium hydroxide solution
4. 4
   ДругоеThe residue obtained
5. 5
   Другоеis purified by chromatography (eluent:heptane)
6. 6
   ДругоеA yellow oil is obtained (m=40.7 g; yield=86%)

Методика

36 g (156 mmol) of 4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 6.5 g (163 mmol) of 60% sodium hydride are added portionwise and the reaction medium is stirred for 1 hour. 25 g (163 mmol) of 2-ethoxyethyl bromide are added portionwise and the medium is stirred at room temperature for 2 hours and then hydrolysed and extracted with ethyl ether. The organic phase is washed with 1N sodium hydroxide solution, and then three times with water. The residue obtained is purified by chromatography (eluent:heptane). A yellow oil is obtained (m=40.7 g; yield=86%).

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