2-Methyl-3-butyn-2-ol → 6-methyl-4,5-heptadien-2-one

HRID 844618Notes

Reaction equation

HRID 844618 reaction equation
[CH3:1][C:2](O)([C:4]#[CH:5])[CH3:3].C[O:8][C:9]([CH3:11])=[CH2:10].CC([O-])=O.[Na+]>C1(C=CC(O)=CC=1)O.CS(O)(=O)=O.CCCCCCC>[CH3:1][C:2]([CH3:3])=[C:4]=[CH:5][CH2:8][C:9](=[O:10])[CH3:11]

Participants

7

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 83002-MethoxypropeneHCID 517045Sodium Acetate

Product 1

HCID 97937556-methyl-4,5-heptadien-2-oneYield 89%

Reagents, catalysts & solvents 3

HCID 785HydroquinoneCatalystHCID 6395Methanesulfonic AcidCatalystHCID 8900HeptaneSolvent

Procedure

21.1 g 2-methyl-3-butin-2-ol, 54.1 g isopropenyl methyl ether, 0.05 g hydroquinone and 100 mL n-heptane were initially introduced into a 500 ml flask. 20.7 mg methanesulfonic acid were added, while stirring. The reaction mixture was stirred under reflux for 6.5 hours. After cooling, it was neutralized with 2 ml methanolic NaOAc solution (10 g/1) and evaporated. After distillation in vacuo, 27.5 g 6-methyl-4,5-heptadien-2-one were obtained, corresponding to a yield of 89%.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 6.5 hours
  3. temperatureAfter cooling
  4. customevaporated
  5. distillationAfter distillation in vacuo

Sources & evidence

ORD record
ord-59e5b4687419485cba2782c8c47d8d23
Source dataset
uspto-grants-2002_04
Patent number
US06380437B1

Reaction notes

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