Acetone → 5-(Hydroxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 65119Notes

Reaction equation

HRID 65119 reaction equation
[C:1](=[O:3])=[O:2].[CH:4]([CH:6]=[C:7]=[O:8])=[O:5].[CH3:9][C:10]([CH3:12])=[O:11]>>[CH3:9][C:10]1([CH3:12])[O:3][C:1](=[O:2])[C:6](=[CH:7][OH:8])[C:4](=[O:5])[O:11]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 280Carbon DioxideHCID 14931171Formyl ketene

Product 1

HCID 111375775-(Hydroxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Procedure

Although the reaction mechanism is unknown, a process may be considered that at an intermediate step of the reaction, carbon dioxide, acetone and formyl ketene as intermediates are formed from formyl Meldrum's acid, and the formyl ketene reacts with the carbonyl compound to give the objective 1,3-dioxin-4-one derivative. In such a process, since the intermediate formyl ketene is extremely reactive, it is considered that resin formation is promoted in the case of high concentration reaction.

Sources & evidence

ORD record
ord-657da6b17bb14ba6b4b1383f972fcad3
Source dataset
uspto-grants-1986_09
Patent number
US04612379

Reaction notes

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