Reaction #1702073

Reaction equation

CAN

cerium ammonium nitrate

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

cerium ammonium nitrate

→

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

Solvents

acetic acid

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. The CAN in the reaction path stands for cerium ammonium nitrate. To 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-methylnaphthalene (b) (202 mg, 1.00 mol) were added acetic acid (8.2 mL) and cerium ammonium nitrate (2.40 g, 4.37 mol) followed by stirring at 100° C. for 1 hour. The reaction solution was poured into ice 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 (15/1) as an elution solvent. The yield was 106 mg (49%).

Source