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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1164285Generated: October 25, 2026

Methanol → 3-Methoxy-1,2,4,5-tetramethylbenzene

https://huagongshe.com/reaction/1164285

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantMethyl iodideHCID 6328—
Reactant2,3,5,6-TetramethylphenolHCID 10694—
ReactantSodium hydrideHCID 24758—
SolventDimethyl SulfoxideHCID 679—
SolventWaterHCID 962—
SolventDiethyl EtherHCID 3283—
Product3-Methoxy-1,2,4,5-tetramethylbenzeneHCID 278664—

Reaction Steps

In 150 ml of DMSO were dissolved 15.0 g of 2,3,5,6-tetramethylphenol and 28 ml of methyl iodide. Under ice-cooling 6.3 g of 60% sodium hydride in oil was added, and the mixture was stirred at room temperature for 1 hour. The excess sodium hydride was decomposed with MeOH and after addition of water extraction with ether was carried out. The extract was dried over sodium sulfate. Removal of the solvent by distillation leaves crystals which were recrystallized from MeOH.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04368150
Source datasetuspto-grants-1983_01
ORD IDord-655501f6e8924ea0b35aba1e4c8912f1
Source noteuspto-grants-1983_01