Selenium Dioxide → 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one

HRID 2297015Notes

Reaction equation

HRID 2297015 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:8])[O:5][C:6]=1[CH3:7].[Se](=O)=[O:10]>O1CCOCC1>[CH3:7][C:6]1[O:5][C:4](=[O:8])[O:3][C:2]=1[CH2:1][OH:10]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 1422104,5-Dimethyl-1,3-dioxol-2-one

Product 1

HCID 105108784-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4,5-dimethyl-2-oxo-1,3-dioxolene (1 mmole) and selenium dioxide (2.5 mmole) in dioxane was heated at reflux for 1 h. Evaporation, extraction and chromatography gave 5-methyl-4-hydroxymethyl-2-oxo-1,3-dioxolene as a yellow oil. TLC: Rf=0.5, 5% MeOH-dichloromethane.

Workup

  1. temperatureat reflux for 1 h
  2. customEvaporation, extraction and chromatography

Sources & evidence

ORD record
ord-4ca4191a926b4872bfdb6c073adf1b29
Source dataset
uspto-grants-2002_12
Patent number
US06489476B1

Reaction notes

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