Reacción #586116

Ecuación de reacción

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

sodium hydride

2-methoxyethyl chloride

→

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

Rendimiento 95.0%

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=42.7 g; yield=95%)

Procedimiento

34 g (148 mmol) of 4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 7.2 g (178 mmol) of 60% sodium hydride are then added portionwise, and the reaction medium is stirred for 1 hour. 16.5 mL (178 mmol) of 2-methoxyethyl chloride are added dropwise, 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=42.7 g; yield=95%).

Fuente