Oxygen → Vanillin

HRID 2308888Notes

Reaction equation

HRID 2308888 reaction equation
C[C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=[O:3].[OH-].[Na+].O=O.[Na].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O>[Cu].[Mn].[Fe]>[O:3]=[CH:2][C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1

Participants

8

Reactant 4

HCID 977OxygenHCID 2214Acetovanillone2×HCID 14798Sodium Hydroxide2×HCID 131715242HCID 131715242, compound

Product 1

HCID 1183Vanillin

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 23930ManganeseCatalystHCID 23978CopperCatalyst

Conditions

Temperature
180 °C

Procedure

Two-gram samples of acetovanillone were separately placed in a batch type reactor vessel with 100 gr of 2N NaOH so that the ratio of NaOH to acetovanillone was 4:1. The reactor vessel was heated to about 180° C. and pressurized with either air or air enriched to 40% oxygen to the pressures indicated in Table 1. The reaction was allowed to proceed for the time indicated in Table 1. In some cases, as indicated in Table 1, sulfates and oxides of the transition elements copper, manganese and iron were employed as catalyst and in one case sodium-m-nitrobenzene sulfonate abbreviated as NAMNO. The resulting oxidation products were analyzed by gas chromatography and yields of vanillin (Van), are reported in Table 1.

Sources & evidence

ORD record
ord-5105c8a16ae749e8b18e11f50c929270
Source dataset
uspto-grants-1987_09
Patent number
US04691061

Reaction notes

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