Reaction #1702069

Reaction equation

5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene

dichloromethane

aluminum chloride

isobutyryl chloride

→

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl isopropyl ketone

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted by ethyl acetate
2. 2
   WashThe organic layer was washed by water
3. 3
   Dryinga saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe crude product was purified by silica gel chromatography

Procedure

The synthesis process is as set forth in the chemical reaction formula below. To 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (188 mg, 1.00 mmol) were added anhydrous dichloromethane (1 mL), aluminum chloride (140 mg, 1.05 mmol), and isobutyryl chloride (112 mg, 1.05 mmol) followed by stirring at room temperature for 3 hours. The reaction solution was poured into cold water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (20/1) as an elution solvent. The yield was 97.4 mg (38%).

Source