p-Toluenesulfonic acid → 3,3,6,6-Tetramethyl-1,4-dioxane-2,5-dione

HRID 342057Notes

Reaction equation

HRID 342057 reaction equation
[OH:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].C1(C)C=CC(S(O)(=O)=[O:15])=CC=1.[C:19]1([CH3:26])[CH:24]=CC=C(C)[CH:20]=1>>[CH3:6][C:2]1([CH3:7])[O:1][C:20](=[O:15])[C:19]([CH3:26])([CH3:24])[O:5][C:3]1=[O:4]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7929M-XyleneHCID 116712-Hydroxyisobutyric acid

Product 1

HCID 812113,3,6,6-Tetramethyl-1,4-dioxane-2,5-dione

Procedure

Crude tetramethyl glycolide was prepared by direct liquid phase synthesis from 2-hydroxy-2-methylpropionic acid using m-xylene as the solvent and p-toluene sulfonic acid as the catalyst. The mixture was refluxed using a Dean-Stark tube to remove water.

Workup

  1. temperatureThe mixture was refluxed
  2. customto remove water

Sources & evidence

ORD record
ord-bf9317ff7c7f414d8e51bf749836759e
Source dataset
uspto-grants-1999_01
Patent number
US05856523

Reaction notes

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