反应详情

To a nitrogen flushed 5 L three neck round bottom flask fitted with a mechanical stirrer, condenser, and a nitrogen inlet was charged 326 g (1.68 mol) of methyl 4-hydoxy-3-n-propylbenzoate, 507.6 g (1.73 mol)of ethyl α-bromo-3,4-methylenedioxyphenylacetate from above, 235 g (1.70 mol) of anhydrous potassium carbonate, and 1.7 L of acetone. The mixture was refluxed with vigorous stirring for 9 hr. The suspension was allowed to cool to ambient temperature and stirred overnight. The mixture diluted with 2 L of ether, cooled to 0° C. and filtered through Super-CelR. The cake washed with ether and the combined filtrate concentrated. The residue was redissolved in ether and the organic layer washed with once with 1 N HCl, saturated sodiuim bicarbonate solution, 10% sodium bisulfite solution, brine, dried with magnesium sulfate, treated with charcoal and filtered through a plug of silica. The pale yellow solution was concentrated to 697.3 g (theoretical 678 g) of a thick yellow oil which was used without purification in the next step. NMR was consistent with the title compound.

1. customTo a nitrogen flushed 5 L three neck round bottom flask
2. customfitted with a mechanical stirrer, condenser, and a nitrogen inlet
3. temperatureThe mixture was refluxed
4. stirringstirred overnight
5. temperaturecooled to 0° C.
6. filtrationfiltered through Super-CelR
7. washThe cake washed with ether
8. concentrationthe combined filtrate concentrated
9. dissolutionThe residue was redissolved in ether
10. washthe organic layer washed with once with 1 N HCl, saturated sodiuim bicarbonate solution, 10% sodium bisulfite solution, brine
11. dry with materialdried with magnesium sulfate
12. additiontreated with charcoal
13. filtrationfiltered through a plug of silica
14. concentrationThe pale yellow solution was concentrated to 697.3 g (theoretical 678 g) of a thick yellow oil which
15. customwas used without purification in the next step