104-61-0Relevant articles and documents
O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols
Jeffrey, Jenna L.,Terrett, Jack A.,MacMillant, David W.C.
, p. 1532 - 1536 (2015)
The efficiency and selectivity of hydrogen atom transfer from organic molecules are often difficult to control in the presence of multiple potential hydrogen atom donors and acceptors. Here, we describe the mechanistic evaluation of a mode of catalytic activation that accomplishes the highly selective photoredox a-alkylation/lactonization of alcohols with methyl acrylate via a hydrogen atom transfer mechanism. Our studies indicate a particular role of tetra-n-butylammonium phosphate in enhancing the selectivity for α C-H bonds in alcohols in the presence of allylic, benzylic, α-C=O, and α-ether C-H bonds.
Conjugate Addition of gem-Borazirconocene Alkenes to Michael Acceptors
Pereira, Schubert,Srebnik, Morris
, p. 1805 - 1808 (1995)
gem-Borazirconocenes, 1, readily add across Michael acceptors in the presence of Cu(I)Br*SMe2, to afford 1,4-addition products in good to excellent yilds.In the case of cycloalkenones diastereomers are produced, with the anti product favored.The selectivity with cyclopentenone is high (9:1), while with cyclohexenone it is less (3:1).In the present context, gem-borazirconocene alkanes can be regarded as α-hydroxyl anion equivalents.
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Nikishin et al.
, (1976)
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Efficient preparation of racemic γ-nonalactone
Tu, Song,Dong, Wan,Yang, Jing,Zhang, Chen,Shen, Youyu
, p. 72 - 74 (2013)
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Characterisation of a by-product formed in the industrial production of γ-nonalactone
Chen, Haitao,Wang, Dan,Liu, Yongguo,Zhang, Guoying,Wang, Tianyi,Wang, Yang,Yang, Shaoxiang,Sun, Baoguo,Tian, Hongyu
, p. 141 - 143 (2016)
Distillation residues from the industrial production of γ-nonalactone, which is accomplished by reaction of hexanol with methyl acrylate initiated by t-butyl peroxide, yielded a by-product which we deduced to be 4-(methoxycarbonylethyl)-γ-nonalactone. The possible pathway of formation of this by-product is discussed.
MELDRUM'S ACID AS A REAGENT FOR THE SYNTHESIS OF 4-ALKANOLIDES
Zav'yalov, S. I.,Ezhova, G. I.,Kravchenko, N. E.
, p. 609 - 612 (1987)
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Identification of Bond-Weakening Spirosilane Catalyst for Photoredox α-C?H Alkylation of Alcohols
Sakai, Kentaro,Oisaki, Kounosuke,Kanai, Motomu
supporting information, p. 337 - 343 (2019/12/24)
The development of catalyst-controlled site-selective C(sp3)?H functionalization is a current major challenge in organic synthesis. This paper describes DFT-guided identification of pentavalent silicate species as a novel bond-weakening catalyst for the α-C?H bonds of alcohols together with a photoredox catalyst and a hydrogen atom transfer catalyst. Specifically, Martin's spirosilane accelerated α-C?H alkylation of alcohols. (Figure presented.).
Production method for synthesizing coconut aldehyde synthetic fragrance through reactive distillation
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Paragraph 0039-0064, (2019/01/08)
The invention belongs to the technical field of fine chemical production, and specifically relates to a production method for synthesizing a coconut aldehyde synthetic fragrance through reactive distillation. The production method comprises the following steps: (a) mixing raw materials through a pipeline so as to obtain a batched mixture; (b) releasing hexanol into a preheater from the interior ofa hexanol high-level tank, and carrying out preheating; (c) pumping the hexanol into the high-boiling-point feeding section of the reaction zone of a reactive distillation tower, pumping the batchedmixture into the low-boiling-point feeding section of the reaction zone of the reactive distillation tower through a dropwise adding pump; (d) separating a crude coconut aldehyde product from the tower bottom of the reactive distillation tower; (e) transferring the hexanol separated in the step (d) into the preheater through a material pump, and allowing the hexanol to continue participating in areaction; and (f) further subjecting the separated crude coconut aldehyde product to separation and purification. The production method provided by the invention adopts a reactive distillation technology to separate by-products namely methanol and tert-butanol and low-boiling-point impurities generated by side reactions out of a reaction system in time, greatly shortens the reaction time, and improves the reaction speed and reaction efficiency.
