2,2,8,8-Tetramethyl-3,6-nonadiyn-5-ol → 2,2,8,8-Tetramethylnona-3,6-diyn-5-one

HRID 484468Notes

Reaction equation

HRID 484468 reaction equation
[CH3:1][C:2]([CH3:14])([C:4]#[C:5][CH:6]([OH:13])[C:7]#[C:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:3]>C1C=CC=CC=1.[O-2].[O-2].[O-2].[Ni+3].[Ni+3]>[CH3:11][C:9]([CH3:12])([C:8]#[C:7][C:6](=[O:13])[C:5]#[C:4][C:2]([CH3:14])([CH3:3])[CH3:1])[CH3:10]

Participants

4

Reactant 1

HCID 113559972,2,8,8-Tetramethyl-3,6-nonadiyn-5-ol

Product 1

HCID 5350942,2,8,8-Tetramethylnona-3,6-diyn-5-one

Reagents, catalysts & solvents 2

HCID 10313272Nickel oxide (Ni2O3)CatalystHCID 241BenzeneSolvent

Procedure

The 2,2,8,8-tetramethyl-nona-3,6-diyn-5-ol prepared in Part A (7.0 g, 36 mmole) was dissolved in 150 mL of benzene, cooled to 5°-10° C. and nickel peroxide (18.15 g, 465 mmole) was added over a period of 20 minutes. After the addition had been completed, the reaction mixture was stirred at room temperature for 30 minutes, then filtered, and the nickel peroxide left on the filter was washed well with benzene and then with dichloromethane. The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene to give 2,2,8,8-tetramethyl-nona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by FAB mass spectroscopy.

Workup

  1. temperaturecooled to 5°-10° C.
  2. additionAfter the addition
  3. filtrationfiltered
  4. waitthe nickel peroxide left on the filter
  5. washwas washed well with benzene
  6. customThe filtrate was evaporated
  7. customto give a yellow solid, which
  8. customwas recrystallized from benzene

Sources & evidence

ORD record
ord-f4cc986354bf4aa49bf8aaa9abefbd1b
Source dataset
uspto-grants-1993_07
Patent number
US05231190

Reaction notes

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