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Relevant academic research and scientific papers

Regioselective Alkylation in the Course of Aldol Condensation under Phase-Transfer Catalytic Conditions

Regio- and stereoselective alkylation in the course of aldol condensation under liquid-solid phase-transfer catalytic conditions, affording conjugated dienyl ether (5) or α-substituted β,γ-olefinic aldehyde (7) depending on the starting halides, both in good yields, was disclosed.The reaction mechanism is also discussed.

SELF-CONDENSATION OF ALDEHYDES

An efficient process useful for the self-condensation of aliphatic aldehydes is provided, catalyzed by dialkylammonium carboxylate salts. In particular, the invention provides a facile method for the preparation of 2-ethyl hexenal via the self-condensation of butyraldehyde using various dialkylammonium carboxylates, e.g., diisopropylammonium acetate or dimethylammonium acetate, as catalyst. Additionally, residual nitrogen arising from the catalyst can be reduced to -100 ppm levels in the product via a simple washing procedure. The invention provides a process for preparing alkenals under conditions which limit the formation of undesired impurities and high-boiling oligomeric substances.

Synthesis of Guerbet ionic liquids and extractants as β-branched biosourceable hydrophobes

This study investigates the synthesis of β-branched amines and β-branched quaternary ammonium chloride ionic liquids as novel extractants. The synthesis methodology was tailored to facilitate the reaction scale-up and the use of biorenewable starting materials. The developed process is an overall green, easy and straightforward synthesis of β-branched amines, and ammonium salts, starting from linear aldehydes. In order to evaluate the potential of the synthesised materials in applications, the rheology, density, thermal stability, chemical stability, phase transitions, and mutual solubility with water of the novel extractants was studied.

CONVERSION OF ALCOHOLS TO LINEAR AND BRANCHED FUNCTIONALIZED ALKANES

Embodiments herein concerns the eco-friendly conversion of simple alcohols to linear or branched functionalized alkanes, by integrated catalysis. The alcohols are firstlyoxidized either chemically or enzymatically to the corresponding aldehydes or ketones, followed by aldol condensations using a catalyst to give the corresponding enals or enones. The enals or enones are subsequently and selectively hydrogenated using a recyclable heterogeneous metal catalyst, organocatalyst or an enzyme to provide linear or branched functionalized alkanes with an aldehyde, keto- or alcohol functionality. The process is also iterative and can be further extended by repeating the above integrated catalysis for producing long-chain functionalized alkanes from simple alcohols.

Vanadium-Catalyzed Condensation of Ethyl Cyanoacetate with Ketones

Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75–100% yield.

Discovery of multicomponent heterogeneous catalysts via admixture screening: PdBiTe catalysts for aerobic oxidative esterification of primary alcohols

In the present study, we demonstrate the utility of "admixture screening" for the discovery of new multicomponent heterogeneous Pd catalyst compositions that are highly effective for aerobic oxidative methyl esterification of primary alcohols. The identification of possible catalysts for this reaction was initiated by the screening of simple binary and ternary admixtures of Pd/charcoal in combination with one or two metal and/or metalloid components as the catalyst. This approach permitted rapid evaluation of over 400 admixture combinations for the oxidative methyl esterification of 1-octanol at 60°C in methanol. Product yields from these reactions varied widely, ranging from 2% to 88%. The highest yields were observed with Bi-, Te-, and Pb-based additives, and particularly from those containing both Bi and Te. Validation of the results was achieved by preparing specific PdBiTe catalyst formulations via a wet-impregnation method, followed by application of response surface methodology to identify the optimal Pd-Bi-Te catalyst stoichiometry. This approach revealed two very effective catalyst compositions: PdBi0.47Te0.09/C (PBT-1) and PdBi0.35Te0.23/C (PBT-2). The former catalyst was used in batch aerobic oxidation reactions with different primary alcohols and shown to be compatible with substrates bearing heterocycle and halide substituents. The methyl ester products were obtained in >90% yield in nearly all cases. Implementation of the PBT-2 catalyst in a continuous-flow packed-bed reactor achieved nearly 60 000 turnovers with no apparent loss of catalytic activity.

Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster

The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti2 and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.

P-Toluene sulfonic acid (PTSA)-MCM-41 as a green, efficient and reusable heterogeneous catalyst for the synthesis of jasminaldehyde under solvent-free condition

This paper reports the synthesis of p-Toluene sulfonic acid (PTSA)-MCM-41 by impregnation method and its characterization XRD, FT-IR, TGA, N2 adsorption-desorption isotherms, SEM, and TEM. The impregnated catalysts were used to catalyse cross-aldol condensation of active methylene bearing aliphatic aldehydes with aromatic aldehydes under solvent and metal-free condition particularly in the synthesis perfumery chemical-jasminaldehyde and related compounds. The as synthesized catalyst PTSA-MCM-41 has displayed high efficiency (selectivity up to 91%) in catalyzing cross-aldol condensation reaction and was reusable (5 cycles) with no apparent loss in activity. The catalytic performance of PTSA-MCM-41 was compared with other catalysts viz., ZnO, proline, proline-LDH, PTSA, PTSA-zirconia and PTSA-zeolite where PTSA-MCM-41 showed better performance particularly in synthesis of jasminaldehyde.

α-Arylation, α-arylative esterification, or acylation: A stoichiometry-dependent trichotomy in the Pd-catalyzed cross-coupling between aldehydes and aryl bromides

Three′s company: The selective α-arylation and α-arylative esterification of linear and branched aldehydes is reported for a variety of bromoarenes. The acylation of aryl bromides can be achieved with linear aldehydes (see scheme). All these transformations were performed with a single [(N-heterocyclic carbene)Pd] catalyst through adjustment of the stoichiometry of the reagents and the appropriate base. Copyright

Alkenylphosphonates: Unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner-Wadsworth-Emmons conditions

Methyl 2-[(diethoxyphosphoryl)methyl]benzoate reacts with several aldehydes to produce an alkenylphosphonate as the major product, together with varying amounts of the expected Horner-Wadsworth-Emmons product, a 1,2-disubstituted E-alkene. Use of a bulky aldehyde or the tert-butyl ester favours the normal HWE product.