6,6-Dimethylhept-2-en-4-yn-1-ol → 6,6-Dimethyl-2-hepten-4-ynal

HRID 580005Notes

Reaction equation

HRID 580005 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[C:3]#[C:4][CH:5]=[CH:6][CH2:7][OH:8]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]([CH3:10])([CH3:9])[C:3]#[C:4][CH:5]=[CH:6][CH:7]=[O:8]

Participants

4

Reactant 1

HCID 534004696,6-Dimethylhept-2-en-4-yn-1-ol

Product 1

HCID 539349696,6-Dimethyl-2-hepten-4-ynalYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To 6,6-dimethyl-2-hepten-4-yn-1-ol (3.56 g, 25.8S mmol) dissolved in 100 ml of freshly distilled methylene chloride was added manganese dioxide (37 g, 425 mmol) and the mixture was stirred for 17 hours. An additional 5.2 g of manganese dioxide was then added and the mixture was stirred for 2 hours, then filtered and washed copiously with methylene chloride. Evaporation of the solvent afforded 2.74 g of 6,6-dimethyl-2-hepten-4-ynal.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. filtrationfiltered
  3. washwashed copiously with methylene chloride
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-894e287bf6fa410994ee57e367ad91fa
Source dataset
uspto-grants-1988_06
Patent number
US04751245

Reaction notes

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