Reaction #586117

Reaction equation

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

Yield 86.0%

Solvents

DMF

Conditions

Workup

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

Procedure

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