HCID 14820155, compound → HCID 15747279, compound

HRID 487075Notes

Reaction equation

HRID 487075 reaction equation
[C:1]([C:4]1[C:5]([OH:13])=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=1)[CH:9]=[O:10])(=[O:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([C:4]1[C:5]([OH:13])=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=1)[CH2:9][OH:10])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14820155HCID 14820155, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15747279HCID 15747279, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

One gram of 5-acetyl-2,4-dihydroxybenzaldehyde was hydrogenated in the presence of 1 g of 10% palladium on carbon in 150 ml of ethanol. After about 1 hour, hydrogen uptake ceased and hydrogenation was terminated. The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in approximately 30 ml of ethyl acetate and cooled in the refrigerator. The resulting solid was recovered by filtration affording 0.66 g of the desired title intermediate, m.p. =151°-152° C. The same reaction when run on a 5-fold scale provide 2.76 g of material.

Workup

  1. customhydrogenation was terminated
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in approximately 30 ml of ethyl acetate
  5. temperaturecooled in the refrigerator
  6. filtrationThe resulting solid was recovered by filtration

Sources & evidence

ORD record
ord-1330e9b8dc9b4fea8cf373953a08fed8
Source dataset
uspto-grants-1994_03
Patent number
US05294613

Reaction notes

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