4-Methylanisole → 4-tert-Butylbenzaldehyde

HRID 265819Notes

Reaction equation

HRID 265819 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[C:10]1([CH3:16])[CH:15]=CC=C[CH:11]=1.[O:17](C1C=CC(C)=CC=1)C1C=CC=CC=1>[Sb].[Cs].[Tl].[V].[P].[K].[Cs].[V].[Co]=O.[Fe]>[C:10]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[O:17])=[CH:7][CH:8]=1)([CH3:16])([CH3:15])[CH3:11]

Participants

5

Reactant 2

HCID 77314-MethylanisoleHCID 19035188HCID 19035188, compound

Product 1

HCID 703244-tert-ButylbenzaldehydeYield 56%

Reagents, catalysts & solvents 2

HCID 131720097HCID 131720097, compoundCatalystHCID 178504103HCID 178504103, compoundCatalyst

Procedure

Higher yields are obtained in the oxidation of methoxy-, phenoxy- or tert-butyl-substituted toluenes, which has been traced back to the positive inductive effect of these groups (Grybowska, 1987; Ueshima, 1992; Constantini, 1986). Thus, p-methoxytoluene and p-phenoxytoluene toluene can be oxidized to the corresponding aldehydes (EP 226 640) at 450° C. on a vanadium-thallium-cesium-antimony catalyst or a vanadium-cesium-potassium-phosphorus-iron-cobalt-oxide catalyst at a yield of over 75%. On the latter catalyst, in accordance with the weaker electron-donating effect of the tert-butyl substituent in comparison with the methoxy and phenoxy substituents, p-tert-butylbenzaldehyde is obtained with a yield of 56% (EP 226 640).

Sources & evidence

ORD record
ord-38742574f75a485f98b6e7b22daca7aa
Source dataset
uspto-grants-1997_07
Patent number
US05648551

Reaction notes

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