Quinoline → 3,4,5-Trimethoxybenzaldehyde

HRID 1733179Notes

Reaction equation

HRID 1733179 reaction equation
C(=O)([O-])OCC[C:5](=[O:18])[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1.[S].N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd]>[CH3:17][O:16][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([O:12][CH3:13])[C:9]=1[O:14][CH3:15])[CH:5]=[O:18]

Participants

6

Reactant 4

HCID 7047QuinolineHCID 5362487SulfurHCID 86737395HCID 86737395, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68583,4,5-TrimethoxybenzaldehydeYield 0.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 28.4 g (10.1 moles) of 3,4,5-trimethoxy-benzoylethyl carbonate in ml 300, prepared as described in step (a), 14.2 g of Pd supported on BaSO4 (10%) and 0.1 ml of a solution of sulfur and quinoline prepared following Rosemund and Zetzsche and diluted 1:3000 are added. The mixture is hydrogenated in a PARR apparatus in an hydrogen atmosphere at ordinary pressure and 25° C. under efficient shaking during 12 hours. The catalyst is removed by filtration and recovered, whereas the organic solution is washed with a 5% NaOH solution and finally evaporated in a vacuum. 17.64 g of 3,4,5-trimethoxybenzaldehyde are obtained, with the same characteristics generally described in the literature.

Workup

  1. customprepared
  2. additiondiluted 1:3000
  3. additionare added
  4. customThe catalyst is removed by filtration
  5. customrecovered, whereas the organic solution
  6. washis washed with a 5% NaOH solution
  7. customfinally evaporated in a vacuum

Sources & evidence

ORD record
ord-d55133f21aff419a9df5055610c6efc3
Source dataset
uspto-grants-1980_12
Patent number
US04240984

Reaction notes

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