Reaktion #586116

Reaktionsgleichung

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

Ausbeute 95.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe medium is stirred at room temperature for 2 hours
2. 2
   Extraktionhydrolysed and extracted with ethyl ether
3. 3
   WaschenThe organic phase is washed with 1N sodium hydroxide solution
4. 4
   SonstigeThe residue obtained
5. 5
   Sonstigeis purified by chromatography (eluent:heptane)
6. 6
   SonstigeA yellow oil is obtained (m=42.7 g; yield=95%)

Vorschrift

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%).

Quelle