Reacción #586117

Ecuación de reacción

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

Rendimiento 86.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente