Catechol → 2,2-Dimethyl-1,3-benzodioxole

HRID 577610Notes

Reaction equation

HRID 577610 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].CO[C:11](OC)([CH3:13])[CH3:12].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:12][C:11]1([CH3:13])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1

Participants

6

Reactant 3

HCID 289CatecholHCID 64952,2-DimethoxypropaneHCID 516892Sodium Bicarbonate

Product 1

HCID 2858692,2-Dimethyl-1,3-benzodioxoleYield 18.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

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).

Workup

  1. temperatureat reflux for 6 h
  2. customAfter reaction
  3. customThe solvent was removed
  4. distillationthe residue was purified by distillation under reduced pressure at 36° C.

Sources & evidence

ORD record
ord-161986bb6e864884bb43625a9a06bb2a
Source dataset
uspto-grants-2015_05
Patent number
US09040556B2

Reaction notes

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