Sodium Acetate → HCID 18690808, compound

HRID 741582Notes

Reaction equation

HRID 741582 reaction equation
[C:1]([C:5]1[CH:6]=[C:7](/[CH:12]=[CH:13]/[CH:14]=[O:15])[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+]>C(O)C.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH2:13][CH:14]=[O:15])[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 18690803HCID 18690803, compound

Product 1

HCID 18690808HCID 18690808, compoundYield 590.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 1.2 g (5.7 mmole) of (E)-3-(3-tert-butyl-5-methylphenyl)-2-propenal in ethanol (20 ml) there were added 5% Pd/C (0.12 g) and sodium acetate (0.12 g, 1.4 mmole). The mixture was hydrogenated at room temperature and atmospheric pressure during 6 h. After filtration of the catalyst, the solvent was evaporated (1.2 g). The raw product was dissolved in CH2Cl2 (20 ml) and a suspension of PCC (0.62 g, 2.8 ml) in CH2Cl2 (20 ml) was added thereto at room temperature. After 2 h, the mixture was diluted in ether (100 ml) filtered on a FLORISIL® column (Fluka) and concentrated (1.2 g). Bulb-to-bulb distillation (80°/10 Pa) provided 3-(3-tert-butyl-5-methylphenyl)propanal (6.88 g, purity>95%, yield 70%).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter filtration of the catalyst
  3. customthe solvent was evaporated (1.2 g)
  4. dissolutionThe raw product was dissolved in CH2Cl2 (20 ml)
  5. additiona suspension of PCC (0.62 g, 2.8 ml) in CH2Cl2 (20 ml)
  6. additionwas added
  7. customat room temperature
  8. waitAfter 2 h
  9. additionthe mixture was diluted in ether (100 ml)
  10. filtrationfiltered on a FLORISIL® column (Fluka)
  11. concentrationconcentrated (1.2 g)
  12. distillationBulb-to-bulb distillation (80°/10 Pa)

Sources & evidence

ORD record
ord-3d2661d61dc54915ab8a3dcde76240b7
Source dataset
uspto-grants-1996_09
Patent number
US05552379

Reaction notes

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