Preparative synthesis of veratraldehyde and citral oxime esters

Дикусар, Е. А.; Zhukovskaya, N. A.; Moiseichuk, K. L.; Zalesskaya, E. G.; Курман, П. В.; Vyglazov, O. G.

doi:10.1134/s1070427208040149

Cited by 6 publications

(7 citation statements)

References 2 publications

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“…For example, veratraldehyde (21b) is a key intermediate for the synthesis of many of the pharmaceuticals such as verazide, amiquinsin, hoqquizil, and so on. 46 To our delight, this heterogeneous photocatalyst exhibited medium to good reactivity towards the mono-substituted styrenes such as Inspired by the excellent reactivity, we were interested to expand the substrates scope only using the heterogeneous photocatalyst (Scheme 3; entries 22b-26b). Besides the model substrate (1a) (see Table 1, entry 3), anethole, trans-methylstyrene, etc.…”

Section: Resultsmentioning

confidence: 99%

A metal-free heterogeneous photocatalyst for the selective oxidative cleavage of CC bonds in aryl olefinsviaharvesting direct solar energy

et al. 2020

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Section: Resultsmentioning

confidence: 99%

A metal-free heterogeneous photocatalyst for the selective oxidative cleavage of CC bonds in aryl olefinsviaharvesting direct solar energy

et al. 2020

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“…In some cases, the corresponding oximes have been proven to present pleasant odour and their easy accessibility from carbonyl compounds was demonstrated. As a consequence, those compounds have been used as olfactory agents in various perfume compositions, instead of the corresponding carbonyl compounds [ 3 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

Conversion of Natural Aldehydes from Eucalyptus citriodora, Cymbopogon citratus, and Lippia multiflora into Oximes: GC-MS and FT-IR Analysis †

et al. 2009

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Three carbonyl-containing extracts of essential oils from Eucalyptus citriodora (Myrtaceae), Cymbopogon citratus (Gramineae) and Lippia multiflora (Verbenaceae) were used for the preparation of oximes. The reaction mixtures were analyzed by GC-MS and different compounds were identified on the basis of their retention times and mass spectra. We observed quantitative conversion of aldehydes to their corresponding oximes with a purity of 95 to 99%. E and Z stereoisomers of the oximes were obtained and separated by GC-MS. During GC analysis, the high temperature in the injector was shown to cause partial dehydratation of oximes and the resulting nitriles were readily identified. Based on FT-IR spectroscopy, that revealed the high stability and low volatility of these compounds, the so-obtained oximes could be useful for future biological studies.

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“…It is extensively used in perfume compounds and formulations, food aromatizers, odorants, and pharmaceutical intermediates. 6 Veratraldehyde can be obtained from Omethylation of vanillin with alkylating agents. The traditional synthesis of O-methylation reactions involved harmful alkylating agents such as dimethyl sulfate, 7 methyl halides, 8 and diazomethane, 9 or nontoxic alkylating agents under harsh conditions, using a solvent such as dimethylformamide.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Veratraldehyde is present in Cymbopogon jevenensis essential oil. It is extensively used in perfume compounds and formulations, food aromatizers, odorants, and pharmaceutical intermediates . Veratraldehyde can be obtained from O-methylation of vanillin with alkylating agents.…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis of Veratraldehyde Using Potassium Promoted Lanthanum–Magnesium Mixed Oxide Catalyst

Molleti

Yadav

2017

Org. Process Res. Dev.

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Veratraldehyde is an important chemical used in perfumery, agrochemical, and pharmaceutical industries. Current processes of manufacture of veratraldehyde use homogeneous catalysts, which make them highly polluting, creating problems of disposal of effluents and product purity. In the current work, veratraldehyde was synthesized from O-alkylation of vanillin with an environmentally benign reagent, dimethyl carbonate. A series of potassium loaded La2O3–MgO were prepared by the incipient wetness impregnation method, and their performance was evaluated vis-à-vis MgO, La2O3, La2O3–MgO, and a series of 1–4 wt % K/La2O3–MgO. All catalysts were characterized by different techniques, such as N2 adsorption/desorption, XRD, TGA-DSC, FT-IR, CO2-TPD, and SEM techniques. The effect of different loadings (1–4 wt %) of potassium on La2O3–MgO was studied, among which 2 wt % K/La2O3–MgO showed the best activity and selectivity due to high dispersion of potassium and high basicity in comparison with the rest. The activity of 2 wt % K/La2O3–MgO in O-methylation of vanillin with dimethyl carbonate (DMC) was closely associated with basicity. Various parameters were studied to achieve the maximum yield of the desired product. The maximum conversion was found with catalyst loading of 0.03 g/cm3 and mole ratio of vanillin and DMC of 1:15 at 160 °C in 2 h. The reaction follows pseudo-first-order kinetics for the O-methylation of vanillin. The energy of activation was found to be 13.5 kcal/mol. Scale-up was done using the kinetic model to observe that the process could be scaled up using the process parameters. The overall process is clean and green.

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Preparative synthesis of veratraldehyde and citral oxime esters

Cited by 6 publications

References 2 publications

A metal-free heterogeneous photocatalyst for the selective oxidative cleavage of CC bonds in aryl olefinsviaharvesting direct solar energy

A metal-free heterogeneous photocatalyst for the selective oxidative cleavage of CC bonds in aryl olefinsviaharvesting direct solar energy

Conversion of Natural Aldehydes from Eucalyptus citriodora, Cymbopogon citratus, and Lippia multiflora into Oximes: GC-MS and FT-IR Analysis †

Green Synthesis of Veratraldehyde Using Potassium Promoted Lanthanum–Magnesium Mixed Oxide Catalyst

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