反応 #79439

反応方程式

1,2,3,4-tetrahydro-1,1,7-trimethyl-naphthalene

potassium bromate

cerium ammonium nitrate

→

title material

収率 89.0%

1,2,3,4-Tetrahydro-4,4,6-trimethyl-1-oxo-naphthalene

収率 89.0%

溶媒

ethyl acetate

water

water

dioxane

反応条件

後処理

1. 1
   その他The organic phase was separated
2. 2
   抽出the aqueous phase extracted with ethyl acetate
3. 3
   洗浄The combined organic extracts were washed with water (2×), saturated sodium bicarbonate and brine
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The residue was purified by silica gel chromatography (6.5×17 cm, 10% ethyl acetate/hexane)

実験手順

A solution of 1,2,3,4-tetrahydro-1,1,7-trimethyl-naphthalene (9.60 g, 55 mmol), potassium bromate (9.17 g, 55 mmol), cerium ammonium nitrate (1.50 g) in water (28 mL) and dioxane (44 mL) was heated under argon at 85° C. for 6 hours. The mixture was then cooled to 0° C., diluted with ethyl acetate and water. The organic phase was separated and the aqueous phase extracted with ethyl acetate. The combined organic extracts were washed with water (2×), saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (6.5×17 cm, 10% ethyl acetate/hexane) to give the title material (9.2 g, 89%) as a colorless oil.

出典