- Selective Monoacetylation of Symmetrical Diols and Selective Monodeacetylation of Symmetrical Diacetates Using HY-Zeolite as Reusable Heterogeneous Catalyst
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HY-Zeolite has been found to be an efficient and reusable catalyst for selective monoacetylation of symmetrical diols and selective monodeacetylation of symmetrical diacetates to form the products in high yields.
- Srinivas,Mahender,Das, Biswanath
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Read Online
- Noncross-linked polystyrene nanoencapsulation of ferric chloride: A novel and reusable heterogeneous macromolecular Lewis acid catalyst toward selective acetylation of alcohols, phenols, amines, and thiols
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Ferric chloride has been successfully nanoencapsulated for the first time on a non-cross-linked polystyrene matrix as the shell material via the coacervation technique. The resulting polystyrene nanoencapsulated ferric chloride was used as a novel and rec
- Alinejad, Sara,Donyapeyma, Ghazaleh,Rahmatpour, Ali
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- An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans
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The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.
- Br?se, Stefan,Koch, Vanessa
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supporting information
p. 3478 - 3483
(2021/07/22)
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- Method of manufacturing [...]
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PROBLEM TO BE SOLVED: To provide a method of practically producing (Z)-14-methylhexadec-8-enal in total 5 processes using inexpensive octane-1,8-diol as a starting raw material and without using pyridinium chlorochromate or hexamethylphosphoric triamide.SOLUTION: A method of producing (Z)-14-methylhexadec-8-enal includes total 5 processed including a first process of monoacetylation of octane-1,8-diol as a starting raw material, a second process of oxidation, a third process of reacting phosphonium salt having a 6-methyloctyl group with ylide generated from a base, a fourth process of carrying out alcoholysis, and a fifth process of oxidation.
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Paragraph 0026
(2019/08/20)
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- A new approach to the synthesis of royal jelly acid
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A new approach to the synthesis of royal jelly acid (trans-10-hydroxy-2- decenoic acid) was proposed starting from 1,8-octanediol, which included selective monoprotection of 1,8-octanediol with acetic anhydride, oxidation, Wittig-Horner reaction, and hydrolysis and acidification, four steps in total, to yield the product. Overall yield is 80.2%.
- Zong, Qian-Shou,Wu, Jian-Yi
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p. 399 - 401
(2014/08/18)
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- A facile synthesis of the sex pheromone of Grapholitha molesta
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The sex pheromone of Grapholitha molesta, (Z/E)-8-dodecylen-1-ol acetate, was easily synthesized in an overall yield of 41.5% with 1,8-octanediol as starting material via mono-esterification, PCC oxidation, and Witting reactions. The Z/E ratio is 83:17. Configuration transformation of Z/E 83:17 compound with sodium nitrite and nitric acid resulted in the production of a compound with Z/E 24:76. The products were confirmed by IR, 1H NMR, and MS spectral data.
- Li, Jiu-Ming,Yong, Jian-Ping,Huang, Feng-Lan,Bai, Shu-Zhen
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experimental part
p. 103 - 105
(2012/07/14)
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- Elaboration of the ether cleaving ability and selectivity of the classical Pearlman's catalyst [Pd(OH)2/C]: Concise synthesis of a precursor for a myo-inositol pyrophosphate
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The cleavage of propargyl, allyl, benzyl, and PMB ethers by Pd(OH) 2/C can be tuned in that order, by varying the reaction conditions. Other moieties such as C-C double bonds, esters, trityl ether, p-bromo and p-nitrobenzyl ethers are stable to these reaction conditions. Cleavage of allyl ethers can be made catalytic by using 1:1 mixture of Pd(OH)2/C and Pd/C. The synthetic potential of the selective ether cleaving ability of Pd(OH)2/C, essentially under neutral conditions, has been demonstrated by an efficient synthesis of a precursor for the preparation of an inositol pyrophosphate derivative.
- Mart, Alson,Shashidhar, Mysore S.
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p. 9769 - 9776,8
(2012/12/11)
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- Elaboration of the ether cleaving ability and selectivity of the classical Pearlman's catalyst [Pd(OH)2/C]: Concise synthesis of a precursor for a myo-inositol pyrophosphate
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The cleavage of propargyl, allyl, benzyl, and PMB ethers by Pd(OH) 2/C can be tuned in that order, by varying the reaction conditions. Other moieties such as C-C double bonds, esters, trityl ether, p-bromo and p-nitrobenzyl ethers are stable to these reaction conditions. Cleavage of allyl ethers can be made catalytic by using 1:1 mixture of Pd(OH)2/C and Pd/C. The synthetic potential of the selective ether cleaving ability of Pd(OH)2/C, essentially under neutral conditions, has been demonstrated by an efficient synthesis of a precursor for the preparation of an inositol pyrophosphate derivative.
- Mart, Alson,Shashidhar, Mysore S.
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p. 9769 - 9776
(2013/01/13)
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- Two approaches to the synthesis of 9-oxo-and 10-hydroxy-2E-decenoic acids, important components of queen substance and royal jelly of honeybees Apis mellifera
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Two approaches to the synthesis of 9-oxo-and 10-hydroxy-2E-decenoic acids, biologically active components of queen substance and royal jelly of honeybees, respectively, were proposed starting with allyl bromide and 1,7-octadiene and using chemo-and regioselective transformations of the common intermediate building block 7-octen-1-ylacetate.
- Ishmuratov,Yakovleva,Tambovtsev,Legostaeva,Kravchenko,Ishmuratova,Tolstikov
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- Process for preparing monoesters
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A process for preparing monoesters comprises the step of reacting at least one diol with at least one carboxylic acid in a biphasic solvent system, the carboxylic acid being sufficiently water soluble to allow esterification to occur, and the biphasic solvent system comprising water and at least one aprotic solvent in which the resulting monoester has greater solubility than in water.
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Page/Page column 4
(2008/06/13)
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- Lipase-catalysed selective monoacylation of 1,n-diols with vinyl acetate
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A simple enzymatic methodology for the selective monoacetylation of 1,n-diols (n=5,8) using vinyl acetate is reported. Monoacetylation excesses of 81-87% at 74-90% 1,n-diol conversions were obtained in toluene and diisopropyl ether using Thermomyces lanuginosus lipase (TLL) immobilised on polypropylene powder as catalyst.
- Framis, Victoria,Camps, Francisco,Clapés, Pere
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p. 5031 - 5033
(2007/10/03)
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- Facile and highly selective monoacylation of symmetric diols adsorbed on silica gel with acetyl chloride
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Monoacetylated alcohols of symmetric 1,n-diols are synthesized quantitatively by refluxing a suspension of the diols adsorbed on silica gel with acetylchloride.
- Ogawa, Haruo,Amano, Misa,Chihara, Teiji
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p. 495 - 496
(2007/10/03)
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- A remarkably simple process for monoprotecting diols
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Lipase from pig pancreas (PPL) has been shown to catalyse selectively the hydrolysis of alkane-1,n-diol bis-acetates into the corresponding monoacetate.
- Houille, Olivier,Schmittberger, Thierry,Uguen, Daniel
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p. 625 - 628
(2007/10/02)
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- Unique Template Effects of Distannoxane Catalysts in Transesterification of Diol esters
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1,n-Diol diacetates (n = 2,3,4) are selectively converted into the corresponding monoacetates by distannoxane-catalyzed transesterification.Such unique selectivity is not encountered with 1,n-diol diacetates where n>/=5.A great difference in reactivity is also seen in the transesterification between methyl butyrate and 1,n-diol monoacetates: the ethylene glycol derivative sluggishly undergoes transesterification whereas higher homologs react smoothly.The unique template effects of the catalysts are discussed in terms of cooperation of two different tin atoms which are located in the proximity.
- Otera, Junzo,Dan-oh, Nobuhisa,Nozaki, Hitosi
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p. 3065 - 3074
(2007/10/02)
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- Highly Selective Monoacylation of Symmetric Diols Catalyzed by Metal Sulfates Supported on Silica Gel
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Several 1,α-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were monoacylated with high selectivity by reaction with esters in the presence of metal sulfates or hydrogen sulfates, like Ce(SO4)2 and NaHSO4, supported on silica gel.Symmetrical secondary diols were also selectively monoformylated, by reaction with ethyl formate.This method of selective esterification is simple and practical.The yield of monoester depends upon both the composition and the volume of the solvent (an ester/alkane mixture).Unsupported NaHSO4 also catalyzed monoacylation, but the selectivity was less than in monoacylations catalyzed by the supported reagent.The selectivity can be explained by the following reasons: (1) monoacylated products are formed selectively because the diol, but not the monoester, is preferentially adsorbed on the surface of the catalysts, where esterification then occurs, and (2) thin diol layers are formed on the surface of the catalysts due to limited solubility of the diols in the solvent.
- Nishiguchi, Takeshi,Kawamine, Katsumi,Ohtsuka, Tomoko
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p. 312 - 316
(2007/10/02)
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- Method of preparing monoesters
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Monoesters of symmetrical dicarboxylic acids and symmetrical diols are prepared in high yield by reacting a diacid or a diol with a monohydric alcohol or monocarboxylic acid, respectively, in an aqueous solution. The resultant monoester is removed from the aqueous solution immediately after its formation by continuous extraction with a nonpolar solvent.
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