Reaction #1563903

Reaction equation

catechol

2,2-Dimethoxypropane

NaHCO3

→

2,2-dimethylbenzo[d][1,3]dioxole

Yield 18.9%

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureat reflux for 6 h
2. 2
   OtherAfter reaction
3. 3
   OtherThe solvent was removed
4. 4
   workup.DISTILLATIONthe residue was purified by distillation under reduced pressure at 36° C.

Procedure

A mixture of catechol (10 g, 91 mmol), 2,2-Dimethoxypropane (8.6 g, 82.6 mmol) and p-TsOH (33 mg, 0.17 mmol) in toluene (100 ml) was stirred at reflux for 6 h. After reaction, the mixture was cooled to room temperature and NaHCO3 was added to neutralize the mixture. The solvent was removed and the residue was purified by distillation under reduced pressure at 36° C. to obtain 2,2-dimethylbenzo[d][1,3]dioxole (2.34 g, 17%) as a yellow oil. 1H NMR (CDCl3-d6) δ 1.69 (s, 6H), 6.78 (m, 4H).

Source