HCID 53774082, compound → HCID 12217345, compound

HRID 1981149Notes

Reaction equation

HRID 1981149 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH:6]=[C:7]([C:13]([CH3:15])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:6][CH:7]([C:13]([CH3:15])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 53774082HCID 53774082, compound

Product 1

HCID 12217345HCID 12217345, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl α-(3,4-dimethoxybenzylidene)acetoacetate (50 g) was catalytically reduced in a Parr low pressure apparatus in ethyl acetate (150 ml) in the presence of 5% palladium on charcoal catalyst (Pd/C)(3 g). The catalyst was removed by filtration; the solvent was removed under reduced pressure; and the residual oil was distilled to give ethyl α-(3,4-dimethoxybenzyl)-acetoacetate (40.5 g, b.p. 162°-164° C./0.4 mm Hg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. distillationand the residual oil was distilled

Sources & evidence

ORD record
ord-ed2640ac62bd4462a47497aac15d599a
Source dataset
uspto-grants-1985_04
Patent number
US04512992

Reaction notes

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