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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2170943Generated: October 30, 2026

Dimethyl Sulfide → 2-Methyl-4-oxo-4H-chromene-8-carbaldehyde

https://huagongshe.com/reaction/2170943

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfideHCID 1068—
ReactantOzoneHCID 24823—
Reactant2-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-oneHCID 57438887—
SolventDichloromethaneHCID 6344—
Product2-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 13374883—

Reaction Conditions

Temperature-60 °C

Reaction Steps

18.5 g (62.8 mmol) of 2-methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one are dissolved in 400 ml of dichloromethane and cooled to −60° C. Ozone is passed into the reaction solution for 30 min. Dimethyl sulfide is then added to the reaction mixture. After warming to room temperature, the solvent is removed in vacuo and the residue is slurried in a little methanol. The solid remaining after filtration is recrystallized from diethyl ether. 9.1 g (77.4% of theory) of the title compound are obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09051316B2
Source datasetuspto-grants-2015_06
ORD IDord-ba717fa48ecd4d1b9b910342c7533413
Source noteuspto-grants-2015_06