Réaction #586117

Équation de réaction

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

Rendement 86.0%

Solvants

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source