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

HRID 844622Notes

Reaction equation

HRID 844622 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.FS(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 87.5%

Reagents, catalysts & solvents 3

HCID 785HydroquinoneCatalystHCID 24603Fluorosulfuric acidCatalystHCID 8900HeptaneSolvent

Conditions

Temperature
68.5 °C

Procedure

25.3 g 2-methyl-3-butin-2-ol, 65.0 g isopropenyl methyl ether, 0.066 g hydroquinone and 120 ml n-heptane were initially introduced into a 500 ml flask under nitrogen. 15.0 mg fluorosulfonic acid were added, while stirring. The mixture was heated to the boiling point and stirred under reflux at 60 to 77° C. for 9 h. After cooling, it was neutralized with 2 ml methanolic NaOAc solution (10 g/1) and evaporated. After distillation, 32.7 g 6-methyl-4,5-heptadien-2-one were obtained, which corresponds to a yield of 87.86.

Workup

  1. temperatureThe mixture was heated to the boiling point
  2. stirringstirred
  3. temperatureAfter cooling
  4. customevaporated
  5. distillationAfter distillation

Sources & evidence

ORD record
ord-2b826d6250804ee2b768251fb1d0ae6e
Source dataset
uspto-grants-2002_04
Patent number
US06380437B1

Reaction notes

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