922-63-4Relevant academic research and scientific papers
Solvent effect on the rate of the Mannich reaction of butyraldehyde with formaldehyde
Marshalok,Karpyak,Makitra,Polyuzhin
, p. 1264 - 1268 (2006)
The Mannich reaction of formaldehyde with butyraldehyde and diethylamine in hydrophilic solvents ensuring homogeneity of the medium follows the kinetic relations typical of an irreversible second-order reaction. The rate constants are determined by the ability of solvents to undergo self-association and their electrophilic solvation power; additional inclusion of the solvent polarity via multiparameter Koppel'-Pal'm equation is necessary to obtain a satisfactory quantitative correlation.
ODORANTS AND COMPOSITIONS COMPRISING ODORANTS
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Page/Page column 24, (2021/10/22)
The present invention relates to new classes of odorous 3-(2- methylenealkoxy)alkanenitrile derivatives of formula (I) which are useful as fragrance or flavor materials in particular in providing dry, woody, dusty, earthy, and/or patchouli notes together with optional coriander, aldehydic, citrus, mandarin, pear, cinnamon, and/ or petal floral-like notes to perfume, aroma or deodorizing/masking compositions.
PREPARING METHOD OF DIMETHYLOLBUTANAL AND PREPERATION METHOD OF TRIMETHYLOLPROPANE USING THE SAME
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Paragraph 0025; 0056-0059; 0073-0079; 0082-0085; 0090, (2021/02/16)
A method for preparing dimethylolbutanal according to one embodiment of the present application comprises the steps of: performing a first aldol reaction with n-butylaldehyde and a first formaldehyde under a first alkylamine catalyst to prepare a first active ingredient including dimethylol butanal and a by-product including ethyl acrolein; performing a distillation process to separate the by-product including the ethyl acrolein; and performing a second aldol reaction with the separated by-product including ethyl acrolein and a second formaldehyde under a second alkylamine catalyst to prepare a second active ingredient including dimethylol butanal.
Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter
Dong, Kaiwu,Li, Huimin,Ren, Xinyi,Shen, Chaoren,Tang, Lin,Wang, Peng
supporting information, p. 3561 - 3566 (2021/05/29)
A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.
Three Ways Aliphatic Aldehydes React with Nonstabilized Azomethine Ylides
Buev, Evgeny M.,Gorbunova, Evgeniya V.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
supporting information, p. 343 - 348 (2020/02/27)
Aliphatic aldehydes readily react with nonstabilized azomethine ylides in one of the three ways to give oxazolidines, pyrrolidines, or Mannich bases, depending on the structure of the starting compound and the reaction conditions. The use of N -(methoxymethyl)- N -[(trimethylsilyl)methyl]benzylamine in DMF provided 5-alkyloxazolidines in 40-97percent yields. On the other hand, three-component reactions of aliphatic aldehydes bearing one α-hydrogen with N -methyl(benzyl)glycine and formaldehyde gives Mannich bases in yields of 47-98percent. A similar reaction of aldehydes bearing branched alkyl groups and two hydrogen atoms at the α-position proceeds as a domino process that gives 3-alkyl-3-formylpyrrolidines in yields of 34-93percent.
Synthetic method of 2-ethylacrylaldehyde
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Paragraph 0013-0020, (2019/01/14)
The invention discloses a synthetic method of 2-ethylacrylaldehyde and belongs to the technical field of organic synthesis. According to the method, n-butanal and formaldehyde are subjected to a reaction for 2-4 h at 40-60 DEG C under catalysis of a di-n-butylamine and B(C6F5)3 mixed system, a reaction liquid is left to stand for layering, an organic layer is taken, 0.1%-0.5% of a polymerization inhibitor is added, a mixture is distilled under normal pressure, a colorless transparent product 2-ethylacrylaldehyde is obtained, and 0.1%-0.5% of the polymerization inhibitor is added for storage. The route is simple to operate, few by-products are produced in the reaction, and the product is high in purity, is not prone to polymerization and has competitive advantage.
The bioinspired design of a reagent allows the functionalization of Cα-H of α,β-unsaturated carbonyl compounds via the Baylis-Hillman chemistry under ambient conditions
Singh, Palwinder,Kumar, Arun,Kaur, Sukhmeet,Kaur, Jagroop,Singh, Harpreet
supporting information, p. 2936 - 2939 (2016/02/20)
A rationally designed reagent capable of affecting alkylation at Cα of α,β-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-bond formation during the reaction play a key role in the working of the reagent.
Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates
Han, Xiaoyu,Dong, Li,Geng, Caiwei,Jiao, Peng
supporting information, p. 3194 - 3197 (2015/07/15)
1,3-Dipolar cycloadditions of triisopropylsilyl nitronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%. (Chemical Equation Presented).
Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons
Ma, Weiwei,Fang, Jie,Ren, Jun,Wang, Zhongwen
supporting information, p. 4180 - 4183 (2015/09/15)
A novel Lewis acid catalyzed formal intramolecular [3 + 3] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters has been successfully developed. This supplies an efficient and conceptually new strategy for construction of bridged bicyclo[2.2.2]octane skeletons. This [3 + 3]IMCC could be run up to gram scale and from easily prepared starting materials. This [3 + 3]IMCC, together with our previously reported [3 + 2]IMCC strategy, can afford either the bicyclo[2.2.2]octane or bicyclo[3.2.1]octane skeletons from the similar starting materials by regulating the substituents on vinyl group.
PROCESS FOR PRODUCTION OF DITRIMETHYLOLPROPANE
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Paragraph 0090-0091, (2014/05/20)
Provided is a method for producing di-TMP by reacting n-butyl aldehyde (NBD), formaldehyde and a base, said method including a first step of reacting the NBD, formaldehyde (1) and a base (I) to obtain a reaction mixture solution containing trimethylolpropane (TMP), di-TMP and 2-ethyl-2-propenal (ECR); a second step of distilling the reaction mixture solution to recover the ECR therefrom; and a third step of sequentially adding the ECR recovered by distillation, and adding at least one of a base (II) and formaldehyde (2), to the reaction mixture solution from which the ECR has been recovered by distillation, and thereby allowing a reaction for production of the di-TMP to proceed gradually, in which TMP is added in any one of the first to third steps or in plural steps of the first to third steps.
