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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2225903Generated: November 2, 2026

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

https://huagongshe.com/reaction/2225903

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-MethylcatecholHCID 340—
ReactantDibromomethaneHCID 3024—
ReactantSodium HydroxideHCID 14798—
CatalystTetrabutylammonium BromideHCID 74236—
SolventWaterHCID 962—
ProductDibromomethaneHCID 3024—
Product4-Methyl-1,3-benzodioxoleHCID 88560111.7%

Reaction Steps

400 g of methylene bromide and 50 g of tetrabutylammonium bromide are taken under reflux in a stirred apparatus and a solution of 400 ml of water, 130 g of sodium hydroxide and 200 g of 3-methylpyrocatechol are added dropwise in the course of 5 hours. At the end of the addition, the mixture is subsequently stirred for a further 2 hours, cooled and extracted with methylene chloride. The organic phase is dried and distilled on a column. After first runnings of unreacted methylene bromide, 175 g of 4-methyl-1,3-benzodioxole are obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05344944
Source datasetuspto-grants-1994_09
ORD IDord-7bcad7d6047b46cf8a67e2791c23f0da
Source noteuspto-grants-1994_09