Vanillin → Catechol

HRID 1703414Notes

Reaction equation

HRID 1703414 reaction equation
O=C[C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1>[Ni]>[C:5]1([O:6][CH3:7])[C:8](=[CH:10][CH:11]=[CH:3][CH:4]=1)[OH:9].[C:5]1([C:8](=[CH:10][CH:11]=[CH:3][CH:4]=1)[OH:9])[OH:6]

Participants

4

Reactant 1

HCID 1183Vanillin

Product 2

HCID 289CatecholHCID 460Guaiacol

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

It is known that aromatic aldehydes decarbonylate when heated over hydrogenation catalysts. Of the aromatic aldehydes containing a phenolic group, vanillin is reported to decarbonylate over nickel at 370°-390° C., giving guaiacol and catechol. It is reported (Synthesis, December, 1969, p. 164) that salicylaldehyde in refluxing toluene and in the presence of a stoichiometric amount of chloro-tris(triphenyl phosphine)-rhodium complex yields phenol in 70% yield.

Workup

  1. temperatureheated over hydrogenation catalysts

Sources & evidence

ORD record
ord-91dee153a6a54f60b357a15d7f8efaa4
Source dataset
uspto-grants-1982_09
Patent number
US04351962

Reaction notes

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