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

HRID 2042890Notes

Reaction equation

HRID 2042890 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-7fec24736bb74912a1b526d469723a6c
Source dataset
uspto-grants-2013_11
Patent number
US08586605B2

Reaction notes

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