3-Methylcatechol → 4-Methyl-1,3-benzodioxole

HRID 1941698Notes

Reaction equation

HRID 1941698 reaction equation
Br[CH2:2]Br.[CH3:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[C:6]=1[OH:12]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH3:4][C:5]1[C:6]2[O:12][CH2:2][O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 3403-MethylcatecholHCID 3024Dibromomethane

Product 1

HCID 885604-Methyl-1,3-benzodioxole

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

11.6 g Adogen 464 and 7 mL of dibromomethane were refluxed in 50 mL of H2O for 0.5 hours under argon. 3-Methylcatechol (8.89 g, 71.6 mmol) was added over 2 hours and the mixture refluxed for an additional 1 hour. Distillation of the product from the reaction mixture afforded the title compound as a yellow oil: HRMS m/e 136.0524 (calc'd for C8H8O2, 136.0524).

Workup

  1. temperaturethe mixture refluxed for an additional 1 hour
  2. distillationDistillation of the product from the reaction mixture

Sources & evidence

ORD record
ord-5e34f1e97774453391337bd86e9ef6b4
Source dataset
uspto-grants-2013_03
Patent number
USRE044048E1

Reaction notes

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