Trifluoromethanesulfonic acid → 3,3-dimethyl-1,4-dioxane-2,5-dione

HRID 1785529Notes

Reaction equation

HRID 1785529 reaction equation
ClC1C=C[CH:5]=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1.FC(F)(F)S(O)(=O)=O>ClCCl>[CH3:5][C:4]1([CH3:3])[C:8](=[O:9])[O:10][CH2:4][C:8](=[O:9])[O:10]1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 102360123,3-dimethyl-1,4-dioxane-2,5-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 g of cyclic keto-ester (7.8 mmol), 2.7 g of metachloroperbenzoic acid (2 eq.) and 70 μl of trifluoromethanesulphonic acid (0.1 eq.) in 20 ml of dichloromethane is left under stirring at ambient temperature for 3 hours. The solvent is eliminated under vacuum, then the medium is analyzed. NMR 1H reveals the complete conversion of the ring with 5 members and the formation of mostly 3,3-dimethyl-2,5-dioxane-1,4-dione (spectroscopic yield: 60%).

Sources & evidence

ORD record
ord-888d8d47fb5c4f5f9649e35e4e8651bf
Source dataset
uspto-grants-2009_03
Patent number
US07504524B2

Reaction notes

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