Acetovanillone → 4-Ethylguaiacol

HRID 2394552Notes

Reaction equation

HRID 2394552 reaction equation
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=O>C(O)C.[Pd].Cl>[CH2:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)[CH3:1]

Participants

5

Reactant 1

HCID 2214Acetovanillone

Product 1

HCID 624654-EthylguaiacolYield 102.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Acetovanillone (Aldrich, 11.0 g, 66 mmol) was dissolved in absolute ethanol (200 ml) and added to 1.5 g of 5% palladium on carbon. A few drops of concentrated hydrochloric acid were added and the mixture hydrogenated on a shaker at 42 psi. The reaction mixture was filtered through Celite, and the filtrate was concentrated to afford 10.3 g of a golden liquid. This was diluted with water, extracted with diethyl ether and the organic phase was washed with water and sodium bicarbonate. The solvent was dried (MgSO4), and concentrated to afford 9.3 g of a slightly yellow liquid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e37b00855b9b46f1ad7c27e3977497f5
Source dataset
uspto-grants-1998_09
Patent number
US05811430

Reaction notes

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