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

HRID 484469Notes

Reaction equation

HRID 484469 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C:15]([CH3:27])([C:17]#[C:18][CH:19]([OH:26])[C:20]#[C:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:16]>CC(C)=O>[CH3:24][C:22]([CH3:25])([C:21]#[C:20][C:19](=[O:26])[C:18]#[C:17][C:15]([CH3:27])([CH3:16])[CH3:14])[CH3:23]

Participants

4

Reactant 2

HCID 113559972,2,8,8-Tetramethyl-3,6-nonadiyn-5-olHCID 131709961Jones' reagent

Product 1

HCID 5350942,2,8,8-Tetramethylnona-3,6-diyn-5-oneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The Jones' reagent (2.2 L) was added dropwise to a solution of 2,2,8,8-tetramethylnona-3,6-diyn-5-ol (500 g, 2.6 mol, prepared in Part A above) in acetone (1.5 L), and the rapid, exothermic reaction which followed was monitored by thin layer chromatography for disappearance of starting material. When this had been observed, the two-phase mixture was poured with agitation into ice/water, and the resultant precipitate was filtered and washed with water until a colorless filtrate was obtained. Air drying afforded 2,2,8,8-tetramethylnona-3,6-diyn-5-one (471 g, 94% yield) as pale yellow crystals which melted at 65°-66° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. customthe rapid, exothermic reaction which
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with water until a colorless filtrate
  4. customwas obtained
  5. customAir drying

Sources & evidence

ORD record
ord-736b9d240bc34c78b8f487297ea33781
Source dataset
uspto-grants-1993_07
Patent number
US05231190

Reaction notes

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