Acetone → Diketene

HRID 1087969Notes

Reaction equation

HRID 1087969 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH3:7][C:8]([CH3:10])=[O:9]>>[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH3:1][C:2]1[O:6][C:8]([CH3:10])([CH3:7])[O:9][C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 12661Diketene

Product 2

HCID 12661DiketeneHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Procedure

Carroll and Bader (M. F. Carroll and A. R. Bader, J. Am. Chem. Soc., Vol. 75, 5400-5402(1953)) disclose the acidcatalyzed reactions of diketene with ketones which yielded 2,2-disubstituted-4-methyl-6-keto-1,3-dioxenes, many reactions of which dioxenes paralleled those of diketene. The adduct of diketene with acetone yielded 2,2,6-trimethyl-1,3-dioxen-4-one (TKD); the reactions of TKD with methanol or 1-butanol to yield methyl acetoacetate or n-butyl acetoacetate are exemplified.

Sources & evidence

ORD record
ord-2e2442b1ef89453bb2ef6927fefa990b
Source dataset
uspto-grants-1990_10
Patent number
US04960924

Reaction notes

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