Reacción #710525

Ecuación de reacción

Allyl bromide

pyrocatechol

Compound A

pyrocatechol

K2CO3

acetone

→

3,4-diallylbenzene-1,2-diol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITThe stirring was continued for another hour
2. 2
   Temperaturathe mixture was refluxed for 5 hours
3. 3
   OtroAfter completion of the reaction
4. 4
   Filtraciónthe solid was filtered
5. 5
   Concentraciónfiltrate was concentrated
6. 6
   Extracciónextracted with chloroform (3×50 mL)
7. 7
   Lavadowashed with brine (1×50 mL)
8. 8
   Secadodried over anhydrous sodium sulfate and solvent
9. 9
   Otrowas removed under reduced pressure
10. 10
    OtroThe reaction mixture was purified by column chromatography (silica gel: 60-120 mesh)
11. 11
    Temperaturawith increasing concentration of chloroform
12. 12
    LavadoElution of 60% and 75% chloroform in petroleum ether yielded pure compounds corresponding to Compound No

Procedimiento

To a solution of pyrocatechol (Compound A) (1 g, 0.009 mol) and dry acetone (10 mL) was added dry K2CO3 (2.646 g, 0.0189 mol) in portions for 30 minutes. The stirring was continued for another hour. Allyl bromide (1.6 mL, 0.0189 mol) was added to the mixture for 30 minutes and the mixture was refluxed for 5 hours. After completion of the reaction, the solid was filtered and filtrate was concentrated and extracted with chloroform (3×50 mL), washed with brine (1×50 mL), dried over anhydrous sodium sulfate and solvent was removed under reduced pressure. The crude material was heated at 175-180° C. for 2 hours. The reaction mixture was purified by column chromatography (silica gel: 60-120 mesh) using petroleum ether with increasing concentration of chloroform. Elution of 60% and 75% chloroform in petroleum ether yielded pure compounds corresponding to Compound No. 2 and Compound No. 3 as liquids respectively.

Fuente