49562-91-6

Upstream product

• 111-71-7 heptanal 
• 100-52-7 benzaldehyde 
• 111-70-6 n-heptan1ol 
• 10032-05-0 1,1-dimethoxyheptane 
• 592-41-6 1-hexene 
• 201230-82-2 carbon monoxide 
• 35770-74-2 Phenoxymagnesium bromide 
• 36359-98-5 ortho-tert-butylphenoxymagnesium bromide 
• 36359-92-9 4-Methylphenoxymagnesiumbromid 
• 36359-99-6 (4-tert-Butylphenoxy)magnesium bromide 
• 66-25-1 hexanal 
• 42768-44-5 2-Bromooctanoyl chloride 
• 71-43-2 benzene 
• 78-93-3 butanone 

Relevant academic research and scientific papers

1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality

Activation of carbonyl moiety is one of the most rudimentary approaches in organic synthesis and is crucial for a plethora of industrial-scale condensation reactions. In esterification and aldol condensation, which represent two of the most important reactions, the susceptibility of the carbonyl group to nucleophile attack allows the construction of a variety of useful organic compounds. In this context, there is a constant need for development of and improvement in the methods for addition-elimination reactions via activation of carbonyl functionality. In this paper, an advanced methodology for the direct esterification of carboxylic acids and alcohols, and for aldol condensation of aldehydes using widely available, inexpensive, and metal-free 1,3-dibromo-5,5-dimethylhydantoin under neat reaction conditions is reported. The method is air- and moisture-tolerant, allowing simple synthetic and isolation procedures for both reactions presented in this paper. The reaction pathway for esterification is proposed and a scale-up of certain industrially important derivatives is performed.

Synthesis of α,β-unsaturated aldehydes based on a one-pot phase-switch dehydrogenative cross-coupling of primary alcohols

An efficient one-pot ruthenium-catalyzed hydrogen-transfer strategy for a direct access to α,β-unsaturated aldehydes has been developed. The employment of enolates prepared in situ from alcohols avoided handling unstable aldehydes and provided a very appealing route to different cinnamaldehydes substituted in position 2. A silica-grafted amine was used as phase-switch tag leading to a selective one-pot process in favor of cross-dehydrogenative coupling products.

Aldol condensation of benzaldehyde with heptanal to jasminaldehyde over novel Mg-Al mixed oxide on hexagonal mesoporous silica

A novel calcined hydrotalcite supported on hexagonal mesoporous silica (CHT/HMS) was synthesized and characterized by XRD, TG-DTA, pore size analysis, SEM-EDAX, and TEM. It possesses high thermal stability, high adsorption capacity and large surface area. 20% (w/w) CHT/HMS was highly active and selective in aldol-condensation of benzaldehyde with heptanal. A kinetic model was developed and validated against experimental data. Jasminaldehyde selectivity of 86% was obtained with heptanal to benzaldehyde mole ratio of 1:5 at 150 °C by using 20% (w/w) CHT/HMS. The results are explained on the basis of the bi-functional character of CHT/HMS, where the role of the weak acid sites is the activation of benzaldehyde by protonation of the carbonyl group which favors the attack of the enolate heptanal intermediate generated on basic sites. The catalyst is stable and reusable.

A selective solvent-free self-condensation of carbonyl compounds utilizing microwave irradiation

An environmentally benign microwave-assisted solvent-free self-condensation of carbonyl compounds was developed using catalytic amounts of triethylamine and lithium perchlorate. Changing the amount of lithium perchlorate helps in controlling the ratio of the single-condensation and double-condensation products. The effect of other additives and microwave activation was also investigated. The optimized conditions were then applied to various cyclic/acyclic ketones and aldehydes, with selectivity observed in many cases.

A green method for the self-aldol condensation of aldehydes using lysine

A self-condensation of aldehydes has been conveniently accomplished by the catalytic action of lysine in water or a solvent-free system under specific emulsion conditions to give α-branched α,β-unsaturated aldehydes in good yields.

Inorganic ammonium salts as catalysts for direct aldol reactions in the presence of water

Inorganic ammonium salts catalyze the direct aldol reaction between unmodified ketones and aldehydes to furnish the corresponding β-hydroxy ketones in aqueous media. The reactions are highly chemoselective and operationally simple.

Synthesis and olfactory evaluation of bulky moiety-modified analogues to the sandalwood odorant polysantol

Five new bulky moiety-modified analogues of the sandalwood odorant Polysantol have been synthesized by aldol condensation of appropriate aldehydes with butanone, deconjugative α-methylation of the resulting α,β-unsaturated ketones, and reduction of the co

Palladium-nanoparticle-catalysed ullmann reactions in ionic liquids with aldehydes as the reductants: Scope and mechanism

An efficient Ullmann-type reductive homocoupling of aryl, vinyl and heteroaryl halides can be promoted by an aldehyde in tetraalkylammonium ionic liquids under very mild reaction conditions. This simple procedure generates symmetrical biaryls under relatively mild conditions. The ionic liquid is crucial for this process because it behaves simultaneously as a base, ligand and reaction medium. The role of the aldehyde is also discussed and a general mechanism for this unusual reaction is proposed. These results open the way to a new efficient method of Pd-catalysed dehydrogenation of carbonyl compounds.

Rhodium(I) complexes with 1′-(diphenylphosphino)ferrocenecarboxylic acid as active and recyclable catalysts for 1-hexene hydroformylation

The rhodium complex trans-[Rh(CO)(Hdpf-κP)(dpf-κ2O, P)] (1), (Hdpf = 1′-(diphenylphosphino)ferrocenecarboxylic acid) was used as an efficient and recyclable catalyst for 1-hexene hydroformylation producing ca. 80% of aldehydes at 10 atm CO/Hsu

Synthesis and sensorial properties of 2-alkylalk-2-enals and 3-(acetylthio)-2-alkyl alkanals

Parallel synthesis was applied to prepare a series of 3-(acetylthio)-2-alkyl alkanals by Michael addition of thioacetic acid under alkaline conditions to α,β-unsaturated 2-alkyl-substituted aldehydes, which were obtained by aldol condensation of the corresponding primary aldehydes as starting materials. The target compounds were characterized in terms of GC, MS, and NMR data. The sensory properties of the odorants, such as odor quality and odor detection threshold value, were determined with a trained panel. Structure-activity relationships are discussed, suggesting that the 1,3-oxygen-sulfur functionality, required for the "olfactophore" of tropical/vegetable notes, can further be extended to the acetylthio derivatives.