- Method for preparing anethol propionaldehyde by anisole
-
The invention relates to the technical field of organic synthesis, in particular to a method for preparing anethoxyl propionaldehyde by anisole, which comprises anisole and 2 - methylallyl diacetate or anisole. 2 - Methacrolein and acetic anhydride were added to the reaction vessel to catalyze the reaction. Then 1 - acetoxy -2 - methyl -3 - (4 - methoxyphenyl) propylene was added to a reaction vessel carrying an alcoholic solvent and an ester exchange catalyst to carry out an ester exchange reaction. The method solves the problems that the cost of anisic aldehyde or anisaldehyde in the product is high due to the expensive price of anisaldehyde or anethol in the prior art, and anisole is synthesized into anethol propionaldehyde. The synthetic anisanylpropanal has a sufficiently high purity. Can be used for perfumery.
- -
-
Paragraph 0050; 0053; 0055; 0058
(2021/10/27)
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- Hydroformylation of natural olefins with the [Rh(COD)(μ-OMe)]2/TPPTS complex in BMI-BF4/toluene biphasic medium: Observations on the interfacial role of CTAB in reactive systems
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The complex [Rh(COD)(μ-OMe)]2 in presence of TPPTS (TPPTS = triphenylphosphinetrisulfonate) was evaluated as catalyst precursor for the in situ hydroformylation of natural olefins (eugenol, estragole and safrole) in biphasic media BMIm-BF4/toluene. Under moderate reaction conditions, the substrates showed the following reactivity order: eugenol > estragole > safrole. The rhodium system showed a high activity and selectivity towards the desired aldehydes. It was found that the use of cetyltrimethylammoniun bromide (CTAB) as phase transfer agent inhibits the hydroformylation reaction. The catalytic phase can be recycled up to four times without evident loss of activity or selectivity. In this work we report the use of an ionic liquid with hydrophilic character, without using water in the reaction medium.
- Baricelli, Pablo J.,Borusiak, Margarita,Crespo, Isis,Melean, Luis G.,Pereira, Juan C.,Rodríguez, Mariandry,Rosales, Merlín
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- Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
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In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
- Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
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supporting information
p. 5699 - 5703
(2019/08/01)
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- Anisole: A further step to sustainable hydroformylation
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Hydroformylation, also known as the "oxo" process, is a major industrial process that employs rhodium or cobalt catalysts in solution; therefore the solvent of this process is a critical issue for its sustainability. Although several innovative solutions have been proposed recently, traditional fossil-derived solvents dominate the scenario for this reaction. In this paper, we studied a series of solvents considered more sustainable in recent ranks in the hydroformylation of a series of olefins. Anisole, a solvent with an impressive sustainability rank and very scarcely exploited in hydroformylation, proved to be an excellent alternative for this reaction.
- Delolo, Fábio G.,Dos Santos, Eduardo N.,Gusevskaya, Elena V.
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supporting information
p. 1091 - 1098
(2019/03/12)
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- Rhodium/Phosphine catalysed selective hydroformylation of biorenewable olefins
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This work reports rhodium catalyzed selective hydroformylation of natural olefins like eugenol, estragole, anethole, prenol and isoprenol using biphenyl based Buchwald phosphine ligands (S-Phos (L1), t-Bu XPhos (L2), Ru-Phos (L3), Johnphos (L4) and DavePhos (L5). Ru-Phos (L3) ligand exhibited high impact on the hydroformylation of eugenol providing high selectivity (90%) of linear aldehyde as major product. In addition, internal natural olefins like anethole and prenol provided moderate to high selectivity (65% and 85% respectively) of branched aldehydes as a major products. The various reaction parameters such as influence of ligands, P/Rh ratio, syngas pressure, temperature, time and solvents have been studied. A high activity and selectivity gained on the way to the linear aldehydes it may be due to the bulky, steric cyclohexyl and isopropoxy groups present in L3 phosphine ligand. Moreover, this catalytic system was smoothly converting natural olefins into corresponding linear and branched aldehydes with higher selectivity under the mild reaction conditions.
- Jagtap, Samadhan A.,Bhanage, Bhalchandra M.
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- A method for preparing finocchio yl-propionaldehyde
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The invention discloses a preparation method of anisyl propionaldehyde. The preparation method comprises that haloid acid is added into anisyl alcohol, the mixture is stirred and undergoes a reaction at a temperature of 5-20 DEG C for 1-3h, a solvent, alkali powder and a phase-transfer catalyst are added into a reactor, a halide and propionaldehyde are slowly added into the reactor, and the materials in the reactor undergo a reaction at a temperature of 60-110 DEG C for 12-16h to produce a product. The anisyl alcohol sold on the market is used as a raw material and reacts with haloid acid to produce p-methoxybenzyl halide, and the p-methoxybenzyl halide, propionaldehyde, sodium hydroxide powder as a base and toluene as a solvent undergo a reaction in the presence of the phase-transfer catalyst to produce anisyl propionaldehyde. The preparation method is economic and environmentally friendly, is free of high pressure reaction equipment and a noble metal catalyst, has a low cost and simple processes, and allows simple reaction conditions.
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-
Paragraph 0038-0040
(2019/02/02)
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- Novel preparation method of anisyl propanal
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The invention relates to a novel preparation method of anisyl propanal. The method comprises the following steps: adding haloid acid into anisyl alcohol, and stirring at 5-20 DEG C to react for 1-3 hours, thereby obtaining the corresponding anisyl halide; and adding a solvent, a solid weak alkali and propenyl methyl ether into a reactor, slowly adding the halide into the reactor, and reacting at 15-25 DEG C for 4-6 hours, thereby obtaining the product. By using the commercially available anisyl alcohol as the raw material, the anisyl alcohol firstly reacts with the haloid acid to obtain the p-methoxy benzyl halogen, and the obtained p-methoxy benzyl halogen reacts with the propenyl methyl ether by using the solid weak alkali as the alkali and an acetonitrile-water mixed solvent as the solvent to obtain the product anisyl propanal. The method is economical and environment-friendly, does not need any high-pressure reactor or noble metal catalyst, is simple to operate, and has the advantages of low cost and mild reaction conditions.
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-
Paragraph 0024; 0025; 0027
(2016/12/01)
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- Support Functionalization with a Phosphine-Containing Hyperbranched Polymer: A Strategy to Enhance Phosphine Grafting and Metal Loading in a Hydroformylation Catalyst
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We present the design of a hydroformylation catalyst through the immobilization of air-stable Rh nanoparticles (NPs) on a magnetic support functionalized with a hyperbranched polymer that bears terminal phosphine groups. The catalyst modification with the hyperbranched polymer improved the metal–support interaction, the metal loading, and the catalytic activity. The catalyst was active for the hydroformylation of natural products, such as estragole, and could be used in successive reactions with negligible metal leaching. The phosphine grafting played a key role in the recyclability of Rh NPs under hydroformylation conditions. The catalytic activity was maintained in successive reactions, even if the catalyst was exposed to air during each recovery procedure. The modification of the support with hyperbranched polyester allowed us either to increase the number of Rh active species or to obtain more active Rh species on the catalyst surface.
- Garcia, Marco A. S.,Heyder, Rodrigo S.,Oliveira, Kelley C. B.,Costa, Jean C. S.,Corio, Paola,Gusevskaya, Elena V.,dos Santos, Eduardo N.,Bazito, Reinaldo C.,Rossi, Liane M.
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p. 1951 - 1960
(2016/07/06)
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- Rh/Cu2O nanoparticles: Synthesis, characterization and catalytic application as a heterogeneous catalyst in hydroformylation reaction
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In this work, we report a rapid protocol for the synthesis of Rh/Cu2O nanoparticles (Rh/Cu2O NPs) in aqueous medium using microwave route. The microwave energy acts as driving force in synthesis which makes the process economical. The obtained nanoparticles were characterized with the help of FEG-SEM, TEM, HRTEM, EDS, XRD, FT-IR and ICP-AES techniques. The prepared Rh/Cu2O nanoparticles gave 100% yield of uniform spherical morphology. This is a simple, inexpensive and time saving protocol for synthesis of Rh/Cu2O nanoparticles than conventional methods. Furthermore, we showed the catalytic application of Rh/Cu2O nanoparticles in hydroformylation reaction for the conversion of 1-hexene to 1-hexanal at mild reaction conditions such as Rh/Cu2O NPs (10 mg), 35 bar pressure of H2/CO at 360 K. The reaction provides 99% conversion and high selectivity (>90%) toward aldehydes with branched aldehyde is a major product. Notably the reaction does not require the any phosphine ligand source, low catalyst loading, low temperature with major advantage of catalyst recyclability.
- Jagtap, Samadhan A.,Bhosale, Manohar A.,Sasaki, Takehiko,Bhanage, Bhalchandra M.
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p. 162 - 168
(2016/12/06)
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- Rhodium catalyzed aqueous biphasic hydroformylation of naturally occurring allylbenzenes in the presence of water-soluble phosphorus ligands
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The rhodium-catalyzed hydroformylation of eugenol was performed in aqueous biphasic systems using various water soluble phosphines: TPPTS (triphenylphosphinetrisulphonated); BDPPETS (bisdiphenylphosphinoethanetetrasulphonated), BDPPPTS (bisdiphenylphosphi
- Baricelli, Pablo J.,Rodriguez, Mariandry,Melean, Luis G.,Alonso, Maria Modro?o,Borusiak, Margarita,Rosales, Merlin,Gonzalez, Beatriz,De Oliveira, Kelley C. B.,Gusevskaya, Elena V.,Dos Santos, Eduardo N.
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p. 163 - 169
(2015/05/05)
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- An efficient TiCl4-catalysed method for the synthesis of para-substituted aromatic aldehydes
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An efficient and highly selective synthesis of para-substituted aromatic aldehydes has been achieved by TiCl4-catalysed Friedel-Crafts alkylation of monosubstituted benzenes with methacrolein diacetyl acetal.
- Zhou, Chenfeng,Su, Weike
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p. 555 - 557
(2015/11/27)
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- Phospholes as efficient ancillaries for the rhodium-catalyzed hydroformylation and hydroaminomethylation of estragole
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The hydroaminomethylation (HAM) of estragole, a bio-renewable starting material, with di-n-butylamine was studied for the first time resulting in three novel amines. The process consists of the alkene hydroformylation followed by the in situ reductive amination of primarily formed aldehydes. In order to control chemo- and regioselectivities, three classes of phosphorus(III) compounds were employed as ancillaries for rhodium(I) catalysts: phosphine, phosphites and phospholes. Phosphole-promoted systems have showed the best overall performance, being more selective in the hydrofomylation step than non-promoted or phosphite-promoted systems, as well as more efficient in the reductive amination step than the standard triphenylphosphine based system. It has been found that both the double bond isomerization (a concurrent reaction) and the enamine hydrogenation (the last step in the HAM process) are favored by less electron-donating ligands, with phospholes presenting an excellent compromise to ensure high chemoselectivity and reasonably fast formation of target amines.
- Oliveira, Kelley C.B.,Carvalho, Sabrina N.,Duarte, Matheus F.,Gusevskaya, Elena V.,Dos Santos, Eduardo N.,Karroumi, Jamal El,Gouygou, Maryse,Urrutigo?ty, Martine
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-
- Rhodium catalyzed aqueous biphasic hydroformylation of naturally occurring allylbenzenes in the presence of water-soluble phosphorus ligands
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The rhodium-catalyzed hydroformylation of eugenol was performed in aqueous biphasic systems using various water soluble phosphines: TPPTS (triphenylphosphinetrisulphonated); BDPPETS (bisdiphenylphosphinoethanetetrasulphonated), BDPPPTS (bisdiphenylphosphi
- Baricelli, Pablo J.,Rodriguez, Mariandry,Melean, Luis G.,Alonso, Maria Modroo,Borusiak, Margarita,Rosales, Merlin,Gonzalez, Beatriz,De Oliveira, Kelley C. B.,Gusevskaya, Elena V.,Dos Santos, Eduardo N.
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p. 163 - 169
(2015/05/06)
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- An electrostatically-anchored rhodium(I) catalyst for the hydroformylation and tandem hydroformylation/acetalization of biorenewable allyl benzenes
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A rhodium catalyst anchored in a commercial anion exchange resin (IRA900/TPPMS/Rh) was prepared straightforwardly through a simple protocol from readily available precursors. The material was used as a heterogeneous catalyst for the hydroformylation and tandem sequence hydroformylation/acetalization of eugenol and estragole under mild conditions. The regioselectivity for linear products was ca. 62percent, but for the allyl benzenes the branched isomer are also valuable. The performance of the anchored catalyst in hydroformylation was comparable to that of the conventional homogeneous rhodium system; however, its efficiency in the acetalization step was significantly higher. The material can be separated from the reaction solutions by decantation and re-used without a significant loss in activity and selectivity. This simple catalytic method represents an economically attractive route to commercially valuable fragrance compounds starting from the substrates easily available from natural bio-renewable sources.
- Carvalho, Glenda A.,Gusevskaya, Elena V.,Santos, Eduardo N. Dos
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p. 2370 - 2377
(2015/04/16)
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- METHOD FOR HYDROFORMYLATION OF UNSATURATED COMPOUNDS
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The invention relates to a method for hydroformylation of unsaturated compounds such as olefins and alkynes using mixtures of synthesis gas (CO/H2), in which either the unsaturated compounds and a catalyst are heated to a reaction temperature of 60 to 200° C. and the synthesis gas is then added, or the unsaturated compounds and the catalyst are brought into contact with pure CO at normal temperature in a preformation step, then are heated to reaction temperature and on reaching the reaction temperature the CO is replaced by the synthesis gas. The pressure is 1 to 200 bar and the CO:H2 ratio in the synthesis gas is in the range from 1:1 to 50:1. The iridium catalyst used comprises a phosphorus-containing ligand in the iridium:ligand ratio in the range from 1:1 to 1:100. With high catalyst activities and low catalyst use, very high turnover frequencies are achieved.
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-
Paragraph 0085
(2014/02/16)
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- Selective hydroformylation of various olefins using diphosphinite ligands
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Novel diphosphinite ligands are synthesized by the reaction of various derivatives of 1,3-diols with chlorodiphenylphosphine. The synthesized ligands exhibited considerable impact on hydroformylation of various olefins with excellent regioselectivity toward branched aldehyde. The effect of solvent, temperature, pressure and catalyst loading on the hydroformylation reaction is also described. The synthesized diphosphinite ligands with rhodium precursor works under milder reaction conditions as compared to traditional phosphine and phosphite-based ligands. Copyright 2013 John Wiley & Sons, Ltd. A novel diphosphinite ligands are synthesized by the reaction of various derivatives of 1,3-diol with chlorodiphenylphosphine. The synthesized ligands exhibited a considerable impact on hydroformylation of various olefins with excellent regioselectivity toward branched aldehyde. The effect of solvent, temperature, pressure and catalyst loading on the hydroformylation reaction is also described. The synthesized diphosphinite ligands with Rhodium precursor works at milder reaction conditions as compared to traditional phosphine and phosphite based ligands. Copyright
- Khan, Shoeb R.,Bhanage, Bhalchandra M.
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p. 313 - 317
(2013/07/04)
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- Vinyl polymerization versus [1,3] O to C rearrangement in the ruthenium-catalyzed reactions of vinyl ethers with hydrosilanes
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Two reactions, vinyl polymerization and [1,3] O to C rearrangement of vinyl ethers, are investigated in the ruthenium-catalyzed reaction with hydrosilanes. The reaction pathways are dependent on the substituents of the vinyl ether, in particular, those of the alkoxy group. Primary-, secondary-, and tertiary-alkyl vinyl ethers, ROCHCH2, are polymerized with ease to give the corresponding polymer in good yields. When R is electron-donating benzyl groups, the reaction does not give the polyvinyl ether but results in [1,3] O to C rearrangement to give the corresponding aldehyde, RCH2CHO in moderate to good yields. The rearrangement selectively proceeds when vinyl ethers having α-substituents are used as the starting materials to give the corresponding ketones in high yields. With catalytic amounts of hydrosilanes, the rearrangement gives ketones or aldehydes selectively. In sharp contrast, use of excess amounts of hydrosilanes leads to the rearrangement followed by reduction of the formed carbonyl group to give the corresponding silyl ethers in good yields. Nature of catalytically active species is discussed. Crown Copyright
- Harada, Nari-Aki,Nishikata, Takashi,Nagashima, Hideo
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supporting information; experimental part
p. 3243 - 3252
(2012/06/01)
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- Biphasic hydroformylation of substituted allylbenzenes with water-soluble rhodium or ruthenium complexes
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The water-soluble complexes [Rh(CO)(Pz)(L)]2 and [HRu(CO)(CH3CN)(L)3][BF4] [L = TPPMS (m-sulfonatophenyl-diphenylphosphine) and TPPTS (tris-m-sulfonato- phenylphosphine)] were used for the first time as catalyst precursors for the hydroformylation of eugenol, estragole, safrole and trans-anethole under moderate conditions in biphasic media. Under mild reaction conditions the substrates showed the following reactivity order: eugenol > estragole ≈ safrole > trans-anethole. The use of cetyl-trimethylammonium chloride (CTAC) as phase transfer agent inhibits the isomerization reaction, reaching high selectivity for the hydroformylation products (80-94%). The catalytic phase can be recycled up to four times with a decrease in the activity over time but maintaining its high selectivity.
- Melean, Luis G.,Rodriguez, Mariandry,Romero, Marynell,Alvarado, Maria L.,Rosales, Merlin,Baricelli, Pablo J.
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experimental part
p. 117 - 123
(2012/01/03)
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- A general and efficient iridium-catalyzed hydroformylation of olefins
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Breaking with conventional wisdom: Hydroformylation catalysts are generally based on rhodium; earlier, cobalt was used. Iridium, which is less expensive than rhodium, was considered too unreactive. However, iridium/phosphine complexes have now been shown to form active catalysts for the hydroformylation of olefins under mild conditions (see scheme; R1, R2=H, alkyl, aryl; R3=H, alkyl). Competing hydrogenation side reactions can be suppressed. Copyright
- Piras, Irene,Jennerjahn, Reiko,Jackstell, Ralf,Spannenberg, Anke,Franke, Robert,Beller, Matthias
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experimental part
p. 280 - 284
(2011/02/28)
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- Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base
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Racemic α-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H- naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-(α- aminobenzyl)-2-naphthol (Betti's base), (ii) an acid promoted crystallization-induced diastereoisomer transformation (CIDT), and (iii) a clean cleavage of the dihydro-1,3-naphthoxazinic ring of the enriched diastereoisomer, easily collected by filtration, allowing the recovery of the enantiomerically enriched aldehydes and the chiral auxiliary.
- Rosini, Goffredo,Paolucci, Claudio,Boschi, Francesca,Marotta, Emanuela,Righi, Paolo,Tozzi, Francesco
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supporting information; experimental part
p. 1747 - 1757
(2011/02/28)
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- Rhodium-catalyzed one-pot hydroformylation-cyclization of allylbenzene derivatives: Simple and efficient route to 5,6-dihydronaphthalenes
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The one-pot hydroformylation-cyclization of allylbenzene derivatives by the catalyst system Rh(CO)2acac/ultranox626/CO/H2/CH2Cl2 led chemoselectively to 5,6-dihydronaphthalene derivatives 5a-d in good yields. The addition of a catalytic amount of H3PO4 enhanced in situ the cyclization process via the nucleophilic attack on the carbonyl group of the linear aldehyde, and finally the elimination of alcohol. The type of substitution on phenyl group of the allylbenzene is of great importance in enhancing the cyclization process.
- Alhaffar, Mouheddin,Suleiman, Rami,Ali, Bassam El
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experimental part
p. 778 - 782
(2010/07/06)
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- Arylation of β-methallyl alcohol catalyzed by Pd(OAc)2 in combination with P(t-Bu)3: application to fragrance synthesis
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Pd(OAc)2 in combination with P(t-Bu)3 catalyzes the coupling of β-methallyl alcohol with 1-bromo-3,4-(methylenedioxy)benzene (1a), 1-bromo-4-methoxybenzene (1b), or 1-bromo-4-tert-butylbenzene (1c). The reaction affords the corresponding 2-methyl-3-aryl-propanals, which are valuable floral fragrances. With 1a or 1b high reaction rates are obtained at 130 °C using NMP/water mixtures and an inorganic base such as Na2CO3. The chemoselectivity of the reaction is almost complete, so that the process appears practically feasible. In contrast, the coupling of β-methallyl alcohol with 1c proceeds with low reaction rates.
- Scrivanti, Alberto,Bertoldini, Matteo,Beghetto, Valentina,Matteoli, Ugo
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p. 543 - 548
(2008/09/16)
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- Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols
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Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzene-disulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts. Georg Thieme Verlag Stuttgart.
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
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p. 3443 - 3452
(2008/02/12)
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- Oxidative coupling of benzenes with α,β-unsaturated aldehydes by the Pd(OAc)2/molybdovanadophosphoric acid/O2 system
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The oxidative coupling reaction of benzene with an α,β- unsaturated aldehyde was examined by the combined catalytic system of Pd(OAc)2 with molybdovanadophosphoric acid (HPMoV) under atmospheric dioxygen. Thus, the reaction of benzene with acrolein under dioxygen (1 atm) by the use of catalytic amounts of Pd(OAc)2 and H4PMo 11VO40·26H2O in the presence of dibenzoylmethane as a ligand in propionic acid at 90 °C for 1.5 h afforded cinnamaldehyde in 59% yield and β-phenylcinnamaldehyde in 5% yield. This catalytic system was extended to the direct oxidative coupling through the C-H bond activation of various arenes with acrolein and methacrolein.
- Yamada, Tomoyuki,Sakaguchi, Satoshi,Ishii, Yasutaka
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p. 5471 - 5474
(2008/04/18)
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- Three-phase microemulsion/sol-gel system for aqueous catalytic hydroformylation of hydrophobie alkenes
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We extended the three-phase transport methodology to the catalytic hydroformylation of alkenes. The method enables to carry out an all-hydrophobic reaction - substrate, product and catalyst - in water. The alkene is microemulsified in the aqueous medium and the solubilized substrate is assumed to be carried to an organometallic rhodium catalyst entrapped within a partially hydrophobicized silica sol-gel matrix. The substrate is then spilled into the porous heterogenized catalyst in which the hydroformylation takes place. The products formed are desorbed from the ceramic material and microemulsified by the same surfactant. Upon breaking of the microemulsion the products are separated. The heterogenized catalyst can be easily separated from the reaction mixture by filtration and be recycled. The hydroformylation process was carried out on various alkenes with reaction yields from ca. 62 to 99%. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Abu-Reziq, Raed,Avnir, David,Blum, Jochanan
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p. 3640 - 3642
(2007/10/03)
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- Functional fragrance precursor
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The present invention relates to a class of fragrance precursor compounds comprising one or more of the compounds derived from the reaction of X—OH and an aldehyde or ketone, said fragrance precursor compounds being of the formula X—O—C(R) (R*) (OR**) wherein R is a C6-24 alkyl group, a C6-24 aralkyl group or a C6-24 alkaryl group; R* is H or a C6-24 alkyl group, a C6-24 aralkyl group or a C6-24 alkaryl group; R** is H or X; X—O representing a moiety derived from X—OH, and wherein X—OH is a compound selected from the group consisting of surfactants, fabric softeners, softener precursor ester amines, softener precursor amido amines, hair conditioners, skin conditions, saccharides and polymers. In a second aspect it relates to a method of preparing such precusors. Further the invention relates to compositions, comprising the precursor of the invention.
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- Electrophilic alkylations in neutral aqueous or alcoholic solutions
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Acid-free Friedel-Crafts chemistry: A paradox? Nucleophilicity scales, based on reactions with benzhydrylium ions, show that many π systems are more nucleophilic than aqueous or alcoholic solutions that are generally employed as solvents for SN1 reactions. Solvolytically generated carbocations can, therefore, be trapped by donor-substituted arenes and alkenes to form products of Friedel-Crafts-type reactions in neutral aqueous solutions (see scheme).
- Hofmann, Matthias,Hampel, Nathalie,Kanzian, Tanja,Mayr, Herbert
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p. 5402 - 5405
(2007/10/03)
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- Arylation of allylic alcohols in ionic liquids catalysed by a Pd-benzothiazole carbene complex
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The reaction of aryl bromides with allylic alcohols catalysed by a Pd-benzothiazole carbene complex, in tetrabutylammonium bromide as solvent, leads principally to β-arylated carbonyl compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Calo, Vincenzo,Nacci, Angelo,Monopoli, Antonio,Spinelli, Michele
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p. 1382 - 1385
(2007/10/03)
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- Palladium-catalyzed arylation of allylic alcohols with aryl iodides in water
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Palladium-catalyzed arylation of allylic alcohols with aryl iodides are shown to occur in the presence of sodium bicarbonate and tetra-n-butylammonium chloride in pure water using palladium acetate as catalyst. β-aromatic carbonyl compounds are obtained in good yields.
- Zhao,Cai,Hu,Song
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p. 3665 - 3669
(2007/10/03)
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