5-Acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione → 2,2,6-Trimethyl-4H-1,3-dioxin-4-one

HRID 65118

Reaction equation

HRID 65118 reaction equation
[CH3:1][C:2]1([CH3:12])[O:11][C:9](=O)[C:6](=CO)[C:4](=[O:5])[O:3]1.[CH3:13]C(C1C(=O)OC(C)(C)OC1=O)=O>C1(C)C=CC=CC=1.C1(C)C(C)=CC=CC=1>[CH3:12][C:2]1([CH3:1])[O:3][C:4](=[O:5])[CH:6]=[C:9]([CH3:13])[O:11]1

Participants

5

Reactant 2

HCID 27634705-Acetyl-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 111375775-(Hydroxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

The derivatives have not heretofore been known at all, but for the first time the present inventors have found a process for producing 2,2-dimethyl-1,3-dioxin-4-one as a compound belonging thereto. Namely, according to the process reported by the present inventors in Chem. Pharm. Bull. 31, (6) 1896 (1983), 2,2-dimethyl-1,3-dioxin-4-one was obtained from formyl Meldrum's acid in the presence of acetone and using a small amount of toluene or xylene as solvent, with a yield of 31%. This formyl Meldrum's acid seems to have a higher reactivity than that of similar acetyl Meldrum's acid. That is, in the case of the latter acid, its thermal decomposition yielded 2,2,6-trimethyl-1,3-dioxin-4-one, whereas in the case of the former acid, its mere heating in the absence of solvent formed only a resinous substance without yielding 2,2-dimethyl-1,3-dioxin-4-one, but when the former acid was heated in a xylene solvent containing acetone, the compound was obtained for the first time. However, its yield was not only low (yield: 31% as described above), but the loss of the raw material acid due to the resin formation was so great that the recovery of the raw material was impossible.

Sources & evidence

ORD record
ord-a85d4adaeea1482e8eaaef23e26844e8
Source dataset
uspto-grants-1986_09
Patent number
US04612379

Linked notes

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