cas 629-76-5, 1-Pentadecanol | Articles data

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New strategy for production of primary alcohols from aliphatic olefins by tandem cross-metathesis/hydrogenation
Primary alcohols are widely used in industry as solvents and precursors of detergents. The classic methods for hydration of terminal alkenes always produce the Markovnikov products. Herein, we reported a reliable approach to produce primary alcohols from terminal alkenes combining with biomass-derived allyl alcohol by tandem cross-metathesis/hydrogenation. A series of primary alcohol with different chain lengths was successfully produced in high yields (ca. 90percent). Computational studies revealed that self-metathesis and hydrogenation of substrates are accessible but much slower than cross-metathesis. This new methodology represents a unique alternative to primary alcohols from terminal alkenes.
Jia, Ruilong,Zuo, Zhijun,Li, Xu,Liu, Lei,Dong, Jinxiang
p. 1525 - 1529
(2019/11/11)

Ru-Photoredox-Catalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids through N-(acyloxy)phthalimide
Decarboxylative aminoxylation of aliphatic carboxylic acid derivatives with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) in the presence of ruthenium photoredox catalysis is reported. The key transformation entails a highly efficient photoredox catalytic cycle using Hantzsch ester as a reductant. The ensuing alkoxyamine can be readily converted to the corresponding alcohol in one pot, representing an alternative approach to access aliphatic alcohols under photoredox conditions.
Zheng, Chao,Wang, Yuting,Xu, Yangrui,Chen, Zhen,Chen, Guangying,Liang, Steven H.
p. 4824 - 4827
(2018/08/24)

Method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation
The invention relates to a method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation. The method comprises the following steps of converting aliphatic carboxylic acid into aliphatic N-(acyl oxy)phthalimide; then, performing photocatalysis decarboxylation reaction to convert the material into aliphatic N-(oxy)2, 2,6,6-tetramethylpiperidine nitrogen-oxygen free radicals; finally, reducing the materials into aliphatic alcohol. The method provided by the invention has the advantages that good chemical selectivity is realized; the wide and easy-to-obtain materialsources are realized. The defects of harsh reaction conditions and high energy consumption such as high temperature and high pressure of aliphatic carboxylic acid conversion by a conventional heat conversion method are avoided; the reaction process is simple and convenient; the operation is easy; the repeated extraction is avoided; in addition, the additional introduction of high-purity hydrogengas is not needed; the reaction energy consumption and the raw material consumption are greatly reduced; the green and environment-friendly effects are achieved; the environment pollution is small; the wide application prospects are realized.
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(2018/11/04)

Convergent synthesis of a deuterium-labeled serine dipeptide lipid for analysis of biological samples
Bacterial serine dipeptide lipids are known to promote inflammatory processes and are detected in human tissues associated with periodontal disease or atherosclerosis. Accurate quantification of bacterial serine lipid, specifically lipid 654 [((S)-15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-l-serine, (3S)-l-serine] isolated from Porphyromonas gingivalis, in biological samples requires the preparation of a stable isotope internal standard for sample supplementation and subsequent mass spectrometric analysis. This report describes the convergent synthesis of a deuterium-substituted serine dipeptide lipid, which is an isotopically labeled homologue that represents a dominant form of serine dipeptide lipid recovered in bacteria.
Dietz, Christopher,Clark, Robert B.,Nichols, Frank C.,Smith, Michael B.
p. 274 - 285
(2017/05/29)

Ruthenium-Catalyzed Deaminative Hydrogenation of Aliphatic and Aromatic Nitriles to Primary Alcohols
The deaminative hydrogenation of nitriles towards alcohols is a useful reaction to transform nitriles into alcohols with NH3 as the sole byproduct. Using the simple and robust RuHCl(CO)(PPh3)3 complex as a catalyst, at low H2 pressures a series of aliphatic and aromatic nitriles could be transformed into the corresponding alcohols. Suitable solvent systems for these reactions were 1,4-dioxane/water and EtOH/water mixtures. In most cases, the selectivity for the alcohols was excellent, and the corresponding amines were formed only in trace amounts.
Molnár, István Gábor,Calleja, Pilar,Ernst, Martin,Hashmi, A. Stephen K.,Schaub, Thomas
p. 4175 - 4178
(2017/10/09)

From alkenes to alcohols by cobalt-catalyzed hydroformylation-reduction
The cobalt-catalyzed hydroformylation of alkenes in the presence of a range of novel cyclic phosphine ligands was investigated. The effect of various parameters such as solvents, additives, cobalt/phosphine ratio, CO/H2 (1:2), and nature of the alkenes was examined. The results revealed that both terminal and internal alkenes are hydroformylated in high yields to give mainly linear products at moderate temperature and syn gas pressure. The linearity ranges from 43 to 85%, with Lim-10 giving the highest proportion of linear product.
Achonduh, George,Yang, Qian,Alper, Howard
supporting information
p. 1241 - 1246
(2015/03/05)

Copper-catalyzed alkyl-alkyl cross-coupling reactions using hydrocarbon additives: Efficiency of catalyst and roles of additives
Cross-coupling of alkyl halides with alkyl Grignard reagents proceeds with extremely high TONs of up to 1230000 using a Cu/unsaturated hydrocarbon catalytic system. Alkyl fluorides, chlorides, bromides, and tosylates are all suitable electrophiles, and a TOF as high as 31200 h-1 was attained using an alkyl iodide. Side reactions of this catalytic system, i.e., reduction, dehydrohalogenation (elimination), and the homocoupling of alkyl halides, occur in the absence of additives. It appears that the reaction involves the β-hydrogen elimination of alkylcopper intermediates, giving rise to olefins and Cu-H species, and that this process triggers both side reactions and the degradation of the Cu catalyst. The formed Cu-H promotes the reduction of alkyl halides to give alkanes and Cu-X or the generation of Cu(0), probably by disproportionation, which can oxidatively add to alkyl halides to yield olefins and, in some cases, homocoupling products. Unsaturated hydrocarbon additives such as 1,3-butadiene and phenylpropyne play important roles in achieving highly efficient cross-coupling by suppressing β-hydrogen elimination, which inhibits both the degradation of the Cu catalyst and undesirable side reactions.
Iwasaki, Takanori,Imanishi, Reiko,Shimizu, Ryohei,Kuniyasu, Hitoshi,Terao, Jun,Kambe, Nobuaki
p. 8522 - 8532
(2015/01/08)

PRODUCTION OF DETERGENT RANGE ALCOHOLS
This invention relates to a process for the production of a mixture of detergent-range alcohols having an average of between 8 and 20 carbon atoms per molecule. The process includes the steps of providing a hydrocarbon stream containing olefins and paraffins in which more than 5% by volume of olefin molecules in the hydrocarbon stream have a total number of carbon atoms which is different from the total number of carbon atoms of the most abundant two carbon numbers of olefins in the hydrocarbon stream; reacting the hydrocarbon stream with CO and an alcohol in the presence of a catalyst in a hydroesterification reaction to form a hydrocarbon stream containing esters and paraffins; separating esters from the hydrocarbon stream containing esters and paraffins; and subjecting the esters to a hydrogenation reaction to provide the mixed alcohol product.
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(2009/01/24)

Metathesis reactions of β-acyloxysulfones: synthesis of 1,6- and 1,7-dienes
A novel alkene-masking strategy has been developed that allows for a metathesis approach to 1,6- and 1,7-dienes. This method was successfully applied to the synthesis of a long-chain alkenone natural product.
O'Neil, Gregory W.,Moser, Daniel J.,Volz, Erasmus O.
supporting information; experimental part
p. 7355 - 7357
(2010/03/01)

Synthesis of symmetrical organic carbonates via significantly enhanced alkylation of metal carbonates with alkyl halides/sulfonates in ionic liquid
We report a new phosgene-free method for the synthesis of symmetrical organic carbonates via alkylation of metal carbonate with various alkyl halides and sulfonates in 1-n-butyl-3-methyl-imidazolium hexafluorophosphate, [bmim] [PF6], as an ecofriendly reaction media. Alkylation of metal carbonate in various ionic liquids with 1-bromo-3-phenylpropane (1a) as a model reactant has thoroughly been investigated. Potassium and cesium carbonates appeared to be the most suitable metal carbonate due to their high solubility in ionic liquids. Besides good to excellent yields, this simple and convenient methodology is devoid of highly toxic and harmful chemicals such as phosgene and carbon monoxide, which is an additional advantage.
Jorapur, Yogesh R.,Chi, Dae Yoon
p. 10774 - 10777
(2007/10/03)

Hydrogenation and Hydrogenolysis with Pd/C in Poly(Ethylene Glycol) (PEG): A Practical and Recyclable Medium
Pd/C in PEG (400) has been found to be an efficient reusable reaction medium for hydrogenation and hydrogenolysis. Both the catalyst and PEG were recycled efficiently over four runs without appreciable loss of activity.
Chandrasekhar,Shyamsunder,Chandrashekar,Narsihmulu
p. 522 - 524
(2007/10/03)

Chemically modified β-cyclodextrins: Efficient supramolecular carriers for the biphasic hydrogenation of water-insoluble aldehydes
Hydrogenation of water-insoluble aldehydes can be achieved in high yields in a genuine two-phase system by using a recoverable catalytic system composed of a water-soluble ruthenium/triphenylphosphine trisulfonate complex and a suitable chemically modified β-cyclodextrin.
Monflier, Eric,Tilloy, Sebastien,Castanet, Yves,Mortreux, Andre
p. 2959 - 2960
(2007/10/03)

A practical decarboxylative hydroxylation of carboxylic acids
Irradiation of esters of N-hydroxy-2-thiazolinethione under air or oxygen at room temperature in the presence of tert-dodecanethiol affords the corresponding nor-alcohols after a reductive work-up.
Barton, Derek H. R.,Gero, Stephane D.,Holliday, Pascale,Quiclet-Sire, Beatrice,Zard, Samir Z.
p. 6751 - 6756
(2007/10/03)

Free-of-loss catalyst recycling in the hydroformylation of higher molecular olefins by a novel process technology
In this paper a novel homogenous-heterogeneous procedure for the hydroformylation reaction of higher molecular olefins is presented, at which the reaction itself is homogeneously catalyzed and only after the reaction the catalyst complex is heterogenized only for separation. This procedure is achieved by using the lithium salt of triphenylphosphine monosulfonic acid (Li-TPPMS) as complex ligand for the hydroformylation catalyst and methanol as solubilizer. Li-TPPMS and its complexes with metal carbonyls are highly soluble in water and methanol, but completely insoluble in almost all other organic solvents. After the reaction the methanol is distilled off. The catalyst system becomes insoluble and can be separated from the reaction product by filtration or by extraction with water. The aqueous catalyst solution is evaporated to dryness and the catalyst system dissolved in methanol for a new reaction. Johann Ambrosius Barth 1997.
Xia, Zhigao,Fell, Bernhard
p. 140 - 144
(2007/10/03)

Hydroformylation with Water- and Methanol-soluble Rhodium Carbonyl/phenyl-sulfonatoalkylphosphine Catalyst Systems - A New Concept for the Hydroformylation of Higher Molecular Olefins
The heterogenization of the homogenous hydroformylating catalyst system enables the recorvery of the catalyst from the reaction products by a simple phase separation but it is unfavourable that many advantages of the homogeneous catalysis are given up by this procedure.To avoid this drawback we used rhodium carbonyl/tert. phosphine catalyst systems soluble as good in methanol as in water for the homogeneously catalyzed hydroformylation of the olefin in methanolic solution.Only after reaction the product mixture is heterogenized by adding water forming an aqueous phase containing the catalyst system.It was shown by the hydroformylation of n-tetradecene-1 with rhodium carbonyl/phenylsulfonatoalkyl-phosphine catalyst systems that this new conception is very useful for the oxo reaction of high-molecular olefins.
Kanagasabapathy, S.,Xia, Zhigao,Papadogianakis, Georgios,Fell, Bernhard
p. 446 - 450
(2007/10/02)

Hydrogenation of carboxylic acids using bimetallic catalysts consisting of Group 8 to 10, and Group 6 or 7 metals
Hydrogenation of carboxylic acids to alcohols was effectively catalyzed by bimetallic systems consisting of Group 8 to 10 late transition-metals, and Group 6 or 7 early transition-metal carbonyls. These catalysts easily converted α,ω-dicarboxylic acid monoesters into ω-hydroxyalkanoic esters in good yields.
He, De-Hua,Wakasa, Noriko,Fuchikami, Takamasa
p. 1059 - 1062
(2007/10/02)

Hair growth composition containing citric acid esters
Triesters of citric acid are used for inducing, maintaining or increasing hair growth. Compositions for topical application to mammalian hair or scalp comprise an effective amount of from 1% to 99% by weight of an ester of citric acid having the structure (1): where, R1, R2 and R3 each independently represent a branched or unbranched alkyl, alkenyl, aryl, alkylaryl or arylalkyl group, each said group having from 1 to 18 carbon atoms, R4 represents -H, or a branched or unbranched saturated or unsaturated acyl, alkyl, aryl, alkylaryl or aylalkyl group having from 1 to 18 carbon atoms, in the presence of a cosmetically acceptable vehicle for the citric acid ester and in the absence of solid absorbent for the ester;, said effective amount of said ester being sufficient to increase hair growth in the rat, when said composition is applied topically thereto over a period of no more than three months, by at least 10% more than that obtainable using a control composition from which the said ester has been omitted, in accordance with the Rat Hair Growth Test.
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(2008/06/13)

DECARBOXYLATIVE PHOTOOXYGENATION OF CARBOXYLIC ACIDS BY THE USE OF ACRIDINE
A new method of decarboxylative photooxygenation of free carboxylic acids is developed by the use of acridine as a light absorber, leading to alcohols after reductive treatment of the photolysate.
Okada, Keiji,Okubo, Katsura,Oda, Masaji
p. 83 - 84
(2007/10/02)

SYNTHESIS OF 20-IODOEICOSANOIK AND 20--IODOEICOSANOIK ACIDS
20-Iodoeicosanoic acid (X) was prepared in 9 steps, its carbon cain being constructed from thiophene and ethyl ester chlorides of dodecanedioic and butanedioic acids.Isotope exchange afforded 20--iodoeicosanoic acid required for scintigraphic studies of the myocardium.Desulfuration of the thiophene precursor VIII was accompanied by formation of side products XI-XIX arising by cleavage of the thiophene C-C bonds.Desulfuration of the model compounds XX and XXI has shown that the formation of these products is general.
Protiva, Jiri,Pecka, Jaroslav,Urban, Jiri,Zima, Jiri
p. 1546 - 1554
(2007/10/02)

THE INVENTION OF RADICAL REACTIONS. PART XVIII. DECARBOXYLATIVE RADICAL ADDITION TO ARSENIC, ANTIMONY, AND BISMUTH PHENYLSULPHIDES - A NOVEL SYNTHESIS OF NOR-ALCOHOLS FROM CARBOXYLIC ACIDS
Carbon centered radicals obtained by decarboxylative transformation of suitable thiohydroxamate esters react with group Va trisphenylsulphides to give intermediates of general formula R-M(SPh)2 (M= As, Sb, Bi).These react spontaneously with air to give the corresponding alcohols.This procedure is especially useful in the case where M=Sb.It is thus sufficient to stir the thiohydroxamate ester with tris(phenylthio)antimony under air to obtain the nor alcohol directly and in high yield.The intermediate organometalloid could also be oxidised with nitrogen dioxide to give the expected nitroalkane albeit in only modest yield.The corresponding organobismuth intermediate derived from 3,3-diphenylpropionic acid could actually be isolated thereby providing strong evidence for the proposed mechanism.
Barton, Derek H. R.,Bridon, Dominique,Zard, Samir Z.
p. 2615 - 2626
(2007/10/02)

THE INVENTION OF NEW RADICAL CHAIN REACTIONS. PART VIII. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS; A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC ACIDS.
The aliphatic and alicyclic esters of N-hydroxy-pyridine-2-thione are readily reduced by tributylstannane in a radical chain reaction to furnish nor-alkanes.In the absence of the stannane a smooth decarboxylative rearrangement occurs to give 2-substituted thiopyridines.The radicals present in this reaction provoke with t-butylthiol an efficient radical reaction with formation of nor-alkane and 2-pyridyl-t-butyl disulphide.Similarly these carbon radicals can be captured by halogen atom transfer to give noralkyl chlorides, bromides and iodides.With oxygen in the presence of t-butylthiol the corresponding noralkyl hydroperoxides are formed in another radical chain reaction.
Barton, Derek H. R.,Crich, David,Motherwell, William B.
p. 3901 - 3924
(2007/10/02)

A Convenient High Yielding Synthesis of Nor-alcohols from Carboxylic Acids
Esters (mixed anhydrides) of carboxylic acids and thiohydroxamic acid (2) react with tris(phenylthio)antimony in the presence of oxygen and water to give high yields of nor-alcohols.
Barton, Derek H. R.,Bridon, Dominique,Zard, Samir Z.
p. 1066 - 1068
(2007/10/02)

Melting Behaviour of Fatty Alcohols and Their Binary Blends
The m.p. of pure fatty alcohols from undecyl to nonadecyl are determined along with those of their corresponding pure fatty acids and their methyl esters ; alternation in m.ps. does not occur in fatty alcohol series unlike the other two.Eutectic formation does not take place in the binary blends of fatty alcohols, but a maximum depression of the m.p. of the lower homologue occurs in presence of 11.0 +/- 1.0 mole percent of higher one in the blend.
Gaikwad, B. R.,Subrahmanyam, V. V. R.
p. 513 - 515
(2007/10/02)

Conversion of Aliphatic and Alicyclic Carboxylic Acids into nor-Hydroperoxides, nor-Alcohols, and nor-Oxo Derivatives using Radical Chemistry
Radicals generated from esters of N-hydroxypyridine-2-thione react smoothly with oxygen in the presence of t-butyl thiol to furnish nor-hydroperoxides, from which the corresponding alcohols and carbonyl derivatives can be readily obtained.
Barton, Derek H. R.,Crich, David,Motherwell, William B.
p. 242 - 244
(2007/10/02)

METHOD FOR DETERMINATION OF ENANTIOMERIC COMPOSITION AND ABSOLUTE CONFIGURATION OF 2,3-DEUTERATED 3-ALKYLPROPANOLS
Assignments were made for diastereotopic methylene protons on C-2 and C-3 of 1-phenyl-3-alkylpropanols in Eu(fod)3-enhanced 1H-NMR spectra to develope a generally applicable method to determine enantiomeric composition and absolute configuration of 2 and/or 3-deuterated 3-alkylpropanols.
Furukawa, Jun,Iwasaki, Shigeo,Okuda, Shigenobu
p. 5257 - 5260
(2007/10/02)

Process for preparing olefins by metathesis of cyclic olefins with acyclic olefins
A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I STR1 wherein R1 and R4 are the same or different from each other and each represents hydrogen, methyl, or ethyl; R2 and R3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; and n represents a whole number from 2 to 12, with an acyclic olefin having the formula II STR2 wherein R5 represents hydrogen, methyl, ethyl or the group STR3 wherein R12 and R13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; Y represents halogen; an acyloxy group R14 --CO--O wherein R14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R15 --O--CO wherein R15 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms; p represents a whole number from 1-12 except when Y is an R14 CO--O group wherein p is from 2 to 12. R6 and R7 are the same or different from each other and each represents hydrogen, methyl, or ethyl; R8 and R9 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; X represents halogen; an acyloxy group R10 --CO--O--, wherein R10 represents alkyl containing 1-12 carbon atoms, phenyl, or phenylalkyl containing 7-12 carbon atoms, or an oxycarbonyl group R11 --O--CO, wherein R11 represents alkyl containing 1-12 carbon atoms, phenyl, or phenylalkyl containing 7-12 carbon atoms, m represents a whole number from 1-12 except when X is an R10 --CO--O-- group wherein m is from 2 to 12 in the presence of a catalytic composition comprising a halogen-tungsten salt and a reducing agent which is an organic tin compound.
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(2008/06/13)