Acetovanillone → 4-Ethylguaiacol

HRID 1739242Notes

Reaction equation

HRID 1739242 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-85ef0dc49cb64af7a6b5b8f834570bf2
Source dataset
uspto-grants-1999_10
Patent number
US05965546

Reaction notes

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