Reaktion #1256502

Reaktionsgleichung

3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene

dimethyl carbonate

sodium methoxide

hydrochloric acid

→

methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate

Ausbeute 88.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux
2. 2
   Einengenwas concentrated under reduced pressure
3. 3
   Sonstigeto remove the organic solvent
4. 4
   Extraktionthe aqueous layer was extracted with ethyl acetate (30 ml×3)
5. 5
   TrocknenThe combined organic layers were dried with anhydrous magnesium sulfate
6. 6
   Einengenwere then concentrated under reduced pressure
7. 7
   EinengenThe objective fractions were concentrated under reduced pressure

Vorschrift

To 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (2.67 g, 9.52 mmol) dissolved in dimethyl carbonate (40 ml) was added sodium methoxide (2.57 g, 47.6 mmol), and the resulting mixture was stirred at reflux with heating (110° C.) for 6 hours. The reaction mixture was mixed with 1 N hydrochloric acid (60 ml) under ice cooling and was concentrated under reduced pressure to remove the organic solvent, and then the aqueous layer was extracted with ethyl acetate (30 ml×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 40 g, ethyl acetate/hexane=1/30). The objective fractions were concentrated under reduced pressure to obtain methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate (2.84 g, 8.39 mmol, 88%).

Quelle