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

HRID 1476721Notes

Reaction equation

HRID 1476721 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-0f088a84fcce41baaa2729bc13579dee
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

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