Reacción #10712

Ecuación de reacción

Catechol

Diethyl dibromomalonate

potassium carbonate

→

benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

Rendimiento 73.2%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed under reduced pressure, and water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   ExtracciónThe residue was extracted with dichloromethane
4. 4
   Lavadothe organic phase was washed with brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   Otroevaporated

Procedimiento

Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, and the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexanes/ethyl acetate, 4:1) gave 3.9 g of benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester. 1H-NMR (CDCl3) δ 6.90–6.97 (m, 4H), 4.37 (q, J=7 Hz, 4H), 1.32 (t, J=7 Hz, 6H).

Fuente