Reaktion #52343

Reaktionsgleichung

7-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Intermediate 8

7-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

acetic acid

acetic acid

→

title compound

Ausbeute 93.0%

6-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one

Ausbeute 93.0%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with diethyl ether (×2)
2. 2
   WaschenThe combined organic phase was washed with water (×1), saturated aqueous sodium bicarbonate (×1) and brine (×1)
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo

Vorschrift

A solution of 7-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Intermediate 8, 1.65 g, 8.7 mmol) in 7.5 mL of glacial acetic acid was cooled to 0° C. and treated with a solution of chromium trioxide (2 g, 20 mmol) in 8mL of acetic acid and 7 mL of water. The reaction mixture was then allowed to warm to ambient temperature and stirred overnight. It was diluted with water and extracted with diethyl ether (×2). The combined organic phase was washed with water (×1), saturated aqueous sodium bicarbonate (×1) and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (1.64 g, 93%) as a yellow oil.

Quelle