Electroorganic synthesis. 4. Facile synthesis of aromatic aldehydes by direct anodic oxidation of p-substituted toluenes

Nishiguchi, Ikuzo; Hirashima, Tsuneaki

doi:10.1021/jo00204a025

Cited by 57 publications

(18 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…10 mg) of tridecane was added as an ''internal standard'' for the gas chromatographic analysis (2 m, 5% C-20M, 50°C Ǟ 200°C; 2 m, 5% Ap-L, 50°C Ǟ 220°C). The peaks of methyl 4-tert-butyl-benzoate, [13] methyl 3-tert-butylbenzoate, [14] and dimethyl 5-tert-butylisophthalate [15] (3a, 3b, and 4, respectively; M ϭ COOCH 3 ) were identified by comparison of their retention times with those of authentic samples and their areas relative to the reference compound were corrected using separately determined calibration factors. The products 3a, 3b, and 4 had formed in 43%, 28%, and 9% yields.…”

Section: Methodsmentioning

confidence: 99%

Dimetalation: The Acidity of Monometalated Arenes Towards Superbasic Reagents

et al. 2001

View full text Add to dashboard Cite

Section: Methodsmentioning

confidence: 99%

Dimetalation: The Acidity of Monometalated Arenes Towards Superbasic Reagents

et al. 2001

View full text Add to dashboard Cite

“…The model reaction is the anodic oxidation of 4-methylanisole (4-methoxy-toluene) to 4-methoxy-benzaldehyde-dimethylacetal. The reaction is important in industrial organic electrochemistry, due to the wide spread of the resulting aldehyde as a precursor and fragrance for fine chemicals production, including pharmaceuticals, dye-stuffs, plating additives, pesticides and flavour ingredients [1][2][3][4].…”

Section: Introductionmentioning

confidence: 99%

A thin-gap cell for selective oxidation of 4-methylanisole to 4-methoxy-benzaldehyde-dimethylacetal

et al. 2007

View full text Add to dashboard Cite

An electrochemical microreactor for organic electrosynthesis has been investigated for the anodic synthesis of 4-methylanisole to 4-methoxy-benzaldehydedimethylacetal in methanol solution. Selectivity and conversion in the single-pass thin-gap flow reactor were examined as a function of the composition of the electrolyte solution, the flow rate and the applied current. The experimental results indicate that potassium fluoride currently used for industrial synthesis and providing higher yields than sodium perchlorate, exerts an influence on the reaction mechanism: high KF concentrations facilitate the undesired oxidation of the diacetal. Nevertheless, a feed solution containing 0.1 M anisole in 0.01 M KF can be converted at 90% in the 100 lm thin-gap cell with acceptable voltages and a measured selectivity of nearly 87%. The selectivity observed substantially higher than that typically observed in conventional electrochemical cells.

show abstract

“…Due to their excellent electrochemical properties, ILs have been used in batteries [17], dye solar cells [18], and fuel cells [19], as well as the electrochemical deposition of metals [20], and electrochemical synthesis [21][22][23]. Direct electro-oxidation is sometimes operationally simpler than indirect electro-oxidation [11,24], and there are some reports concerning about the direct electro-oxidation of CAH bonds to form aldehydes [8,10,11], but to our knowledge no report describes the process in a semi-aqueous IL reaction medium. In keeping with our continuing efforts to utilize direct electro-oxidation in organic synthesis, we now report the direct electro-oxidative synthesis of aromatic aldehydes in aqueous imidazole IL solutions, thereby providing a new ''green method'' for the production of aromatic aldehydes.…”

Section: Introductionmentioning

confidence: 99%