Acetovanillone → 4-Ethylguaiacol
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
Product 1
Reagents, catalysts & solvents 3
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
- filtrationThe reaction mixture was filtered through Celite
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-3151ed57c0d4466eaf2c0aade4f7d137
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05624927
Reaction notes
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