Reaction #710525

Reaction equation

Allyl bromide

pyrocatechol

Compound A

pyrocatechol

K2CO3

acetone

→

3,4-diallylbenzene-1,2-diol

Conditions

Workup

1. 1
   workup.WAITThe stirring was continued for another hour
2. 2
   Temperaturethe mixture was refluxed for 5 hours
3. 3
   OtherAfter completion of the reaction
4. 4
   Filtrationthe solid was filtered
5. 5
   Concentrationfiltrate was concentrated
6. 6
   Extractionextracted with chloroform (3×50 mL)
7. 7
   Washwashed with brine (1×50 mL)
8. 8
   Dryingdried over anhydrous sodium sulfate and solvent
9. 9
   Otherwas removed under reduced pressure
10. 10
    OtherThe reaction mixture was purified by column chromatography (silica gel: 60-120 mesh)
11. 11
    Temperaturewith increasing concentration of chloroform
12. 12
    WashElution of 60% and 75% chloroform in petroleum ether yielded pure compounds corresponding to Compound No

Procedure

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.

Source