Methyl vinyl ketone → Piperitenone

HRID 1657545Notes

Reaction equation

HRID 1657545 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+]>C(O)(=O)C>[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 176Acetic AcidSolvent

Procedure

70 g of methyl vinyl ketone are added dropwise in the course of 60 minutes, whilst stirring, to 1,000 g of mesityl oxide and 50 ml of 50% potassium hydroxide solution, at 70°C. Thereafter the mixture is stirred for a further 10 minutes at 70°C and neutralized with glacial acetic acid, and the organic phase is distilled. 181 g of crude piperitenone are obtained; piperitenone content 55.7%, yield therefore 67.2%.

Workup

  1. distillationthe organic phase is distilled

Sources & evidence

ORD record
ord-975418a9ba7c42b880273ee5e0ff21a4
Source dataset
uspto-grants-1976_06
Patent number
US03960970

Reaction notes

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