Palladium Chloride → Bis(dibenzylideneacetone)palladium

HRID 2259942Notes

Reaction equation

HRID 2259942 reaction equation
[Pd:1](Cl)Cl.C([O-])(=O)C.[Na+].[CH:9](=[CH:16][C:17]([CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[CH:24]1[CH:23]=[CH:22][C:21](/[CH:20]=[CH:19]/[C:17](/[CH:16]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])=[CH:26][CH:25]=1.[CH:24]1[CH:23]=[CH:22][C:21](/[CH:20]=[CH:19]/[C:17](/[CH:16]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])=[CH:26][CH:25]=1.[CH:24]1[CH:23]=[CH:22][C:21](/[CH:20]=[CH:19]/[C:17](/[CH:16]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])=[CH:26][CH:25]=1.[Pd:1].[Pd:1]

Participants

5

Reactant 3

HCID 24290Palladium ChlorideHCID 95417Dibenzylidene acetoneHCID 517045Sodium Acetate

Product 1

HCID 9811564Bis(dibenzylideneacetone)palladium

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

1.05 g palladium chloride were added to a 100 mL methanol solution containing 3.9 g sodium acetate and 4.6 g dibenzylideneacetone. The reaction mixture was warmed to 55° C. and the temperature maintained for one hour so that a precipitate was formed. The precipitate was then filtered from the methanol and redissolved in chloroform to produce a dark purple solution. This solution was stripped under reduced pressure at 25°-30° C. to produce a dark purple or black solid of Pd2DBA3.CHCl3. 1.5 g of the solid was dissolved in 100 mL THF, and added to a solution of 140-150 g of 30-5 NBR in 1.1-1.2 L THF. After 22 hours at 75°-90° C. and 350 psi hydrogen, a sample was withdrawn and a cast film IR analysis indicated that 63 percent of the olefinic NBR unsaturation had been hydrogenated.

Workup

  1. temperaturethe temperature maintained for one hour so that a precipitate
  2. customwas formed
  3. filtrationThe precipitate was then filtered from the methanol
  4. dissolutionredissolved in chloroform
  5. customto produce a dark purple solution
  6. customwas stripped under reduced pressure at 25°-30° C.

Sources & evidence

ORD record
ord-3f566688feec474a910ce1b72b40ee40
Source dataset
uspto-grants-1995_12
Patent number
US05475121

Reaction notes

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