Reaction #1702071

Reaction equation

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-methylnaphthalene

potassium permanganate

sodium hydroxide

KMnO4

potassium permanganate

→

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenecarboxylic acid

Solvents

pyridine

Conditions

Workup

1. 1
   FiltrationThe reaction solution was filtrated by celite
2. 2
   workup.ADDITIONby adding hydrochloric acid
3. 3
   ExtractionAfter extraction by ethyl acetate
4. 4
   Dryingthe liquid was dried over magnesium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe crude product was purified by silica gel chromatography

Procedure

The synthesis process is as set forth in the chemical reaction formula below. The KMnO4 in the reaction path stands for potassium permanganate. To 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-methylnaphthalene (3.52 g, 17.4 mmol) were added pyridine (12 mL), potassium permanganate (6.70 g, 42.4 mmol), and sodium hydroxide (1.00 g, 25.0 mmol) followed by stirring at 95° C. for 5 hours. The reaction solution was filtrated by celite and the filtrate was made acidic by adding hydrochloric acid. After extraction by ethyl acetate, the liquid was dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (4/1) as an elution solvent. The yield was 141.6 mg (3%).

Source