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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1903127Generated: November 2, 2026

Methyl iodide → 4-Methoxymethyl-1-tosylindole

https://huagongshe.com/reaction/1903127

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantPotassium HydroxideHCID 14797—
Reactant[1-(4-Methylbenzene-1-sulfonyl)-1H-indol-4-yl]methanolHCID 12553826—
CatalystTetrabutylammonium hydrogen sulfateHCID 94433—
SolventDichloromethaneHCID 6344—
Product4-Methoxymethyl-1-tosylindoleHCID 13136276—

Reaction Steps

3rd stage: In sequence, 27 g of pulverulent potassium hydroxide, 27 ml of methyl iodide and 2.7 g of tetrabutyl-ammonium-hydrogen-sulfate are added to a solution of 13.5 g of 4-hydroxymethyl-1-tosylindole in 400 ml of methylene chloride. The substance is strongly agitated for 24 h. Then, it is filtered off of the potassium hydroxide, washed neutral with water, and the solvent is distilled off. The raw product (16.46 g) is crystallized out of diisopropylether. 12.2 g of 4-methoxymethyl-1-tosylindole with a m.p. of 85.5°-89° C. is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04435403
Source datasetuspto-grants-1984_03
ORD IDord-5829b66794824e14a7b764835c0d7c28
Source noteuspto-grants-1984_03