2,2,8,8-Tetramethyl-3,6-nonadiyn-5-ol → 2,2,8,8-Tetramethylnona-3,6-diyn-5-one
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
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 7.5 °C
Procedure
The 2,2,8,8-tetramethylnona-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, 200 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-tetramethylnona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by fast atom bombardment (FAB) mass spectroscopy.
Workup
- additionAfter the addition
- filtrationfiltered
- waitthe nickel peroxide left on the filter
- washwas washed well with benzene
- customThe filtrate was evaporated
- customto give a yellow solid, which
- customwas recrystallized from benzene
Sources & evidence
- ORD record
- ord-969fe95dd5ec4ffe8d68ddd0da54b220
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06482950B1
Reaction notes
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