Acetic Acid → 3,5-Dioxohexanoic acid

HRID 1620362Notes

Reaction equation

HRID 1620362 reaction equation
C1C=[C:5]2[C:7]([C:9](O)(O)[C:10](=[O:11])C2=CC=1)=[O:8].[C:14]([OH:17])(=[O:16])[CH3:15]>[OH-].[OH-].[Pd+2]>[CH3:5][C:7]([CH2:9][C:10]([CH2:15][C:14]([OH:17])=[O:16])=[O:11])=[O:8]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 10236Ninhydrin

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Compound 77 (0.302 g, 0.44 mmol) was dissolved in glacial acetic acid (20 mL). Pd(OH)2 (80 mg) was added and the mixture was charged with H2 (160 psi) in a Parr hydrogenator and stirred over night at room temperature. The reaction was found to be complete according to TLC (product stains bright purple after staining with ninhydrin). Pd(OH)2 was filtered off and the solvent was removed in vacuo to afford the pure product 78 as the triacetate salt.

Workup

  1. additionthe mixture was charged with H2 (160 psi) in a Parr hydrogenator
  2. filtrationPd(OH)2 was filtered off
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f930969a3f0746cdbae09a89bfa0b191
Source dataset
uspto-grants-2014_07
Patent number
US08772446B2

Reaction notes

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