Methyl vinyl ketone → Piperitenone

HRID 1657541

Reaction equation

HRID 1657541 reaction equation
[CH:1]([C:3]([CH3:5])=O)=[CH2:2].O=[C:7]([CH:9]=[C:10]([CH3:12])[CH3:11])[CH3:8].[OH-:13].[K+]>O1CCCC1>[CH3:5][C:3]1[CH2:8][CH2:7][C:9](=[C:10]([CH3:12])[CH3:11])[C:2](=[O:13])[CH:1]=1

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 8858Mesityl oxideHCID 14797Potassium Hydroxide

Product 1

HCID 381152Piperitenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Furthermore, J. J. Beereboom (U.S. Pat. No. 3,238,261 and J. Org. Chem., 31, 2026 (1966)) describes the reaction of methyl vinyl ketone with excess mesityl oxide in the presence of potassium hydroxide powder in tetrahydrofuran as the solvent. The piperitenone obtained is purified in a very expensive manner via the piperitenone-bisulfite adduct. In this process, yields of piperitenone of between 36 and 54% of theory are obtained.

Sources & evidence

ORD record
ord-d28f9dc415d6496bb51c4d7048fe8eb8
Source dataset
uspto-grants-1976_06
Patent number
US03960970

Linked notes

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