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METHOD FOR PRODUCING ALCOHOL BY HYDROGENATING LACTONE AND CARBOXYLIC ACID ESTER IN LIQUID PHASE

Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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alpha-trifluoromethylation of secondary and sterically hindered carboxylates with use of BrF3

Secondary esters and those with sterical hindrance at the beta carbon were reacted with base, carbon disulfide, and methyl iodide to produce methyl 2-carboalkoxydithioalkenoate (2). These compounds were reacted with BrF 3, forming the corresponding alpha-trifluoromethyl esters (3) along with 1,1-difluoro-2-trifluoromethyl-2-alkyl ethers (4). The products of type 4 have been transformed to derivatives of type 3, thus raising the overall yields of the target respective alpha-trifluoromethyl esters to 65-80%. The reaction is tolerant to different functional groups such as halogens, protected alcohols, esters, and lactones.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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A 4 – methyl piperidine -3 – one and its derivatives simple method for preparing (by machine translation)

The invention relates to a 4 – methyl piperidine – 3 – one and its derivatives simple preparation method. This invention utilizes the alpha – methyl – gamma – butyrolactone and nitromethane reaction preparation 1 – nitro – 3 – methyl – 5 – hydroxy-n-pentyl – 2 – one, then by the sulfonyl chloride reagent for protecting hydroxyl to obtain 1 – nitro – 3 – methyl – 5 – protection […] – 2 – one, by hydrogenation reduction of nitro to amino, cyclization to obtain at the same time 4 – methyl piperidine – 3 – one. The invention also provides by 4 – methyl piperidine – 3 – one for the preparation of 2 – chloro – 3 – amino – 4 – methyl pyridine, N – benzyl – 4 – methyl piperidine – 3 – ones. The present invention the used raw materials are cheap and easily obtained, mild condition, operation is simple and safe, high reaction selectivity, high product yield and purity, low cost, less wastes, and environmental protection. (by machine translation)

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Multifunctional Cascade Catalysis of Itaconic Acid Hydrodeoxygenation to 3-Methyl-tetrahydrofuran

Hybrid production of isoprene from biomass-derived sugar as a feedstock for renewable rubber is a three-part process comprising glucose fermentation to itaconic acid, liquid-phase hydrodeoxygenation to 3-methyl-tetrahydrofuran, followed by vapor-phase dehydra-decyclization to isoprene. Here, we investigate a multifunctional catalyst design for itaconic acid hydrodeoxygenation to 3-methyl-tetrahydrofuran. The production of 3-methyl-tetrahydrofuran from itaconic acid is a multistep process involving hydrogenation, acid-catalyzed dehydration, and hydrodeoxygenation of multiple organic functionalities. A detailed kinetic analysis of this multistep reaction network over a Pd/C catalyst revealed a kinetic bottleneck in the reduction of methyl-gamma-butyrolactone to 1,4-methylbutanediol, which was accelerated through the use of Re as an oxophillic promoter. Varying ratios of Pd:Re indicated a maximum overall rate of lactone ring opening with a 3.5:1.0 Pd:Re ratio, likely due to the combined capability of Pd to hydrogenate double bonds and Re to open the lactone ring. Applying this insight, the overall rate of itaconic acid hydrodeoxygenation to 3-methyl-tetrahydrofuran increased by more than an order of magnitude.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Synthesis of antimalarial G-factors endoperoxides: relevant evidence of the formation of a biradical during the autoxidation step

In the search for new antimalarial endoperoxides related to G-factors series, using a methodology based on autoxidation of a dienol sytem, unexpected cyclic ether alcohols and hydroperoxides were obtained confirming the structure of the previously postulated biradical intermediate implicated in oxygen uptake. Antimalarial activities of PMB-endoperoxides are greatly enhanced when the peroxyhemiketal function is methylated for the G3 endoperoxide.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Reactions of unsaturated amides under hydroformylation conditions

N,N-diethyl methacrylamide (1) undergoes hydroformylation, followed by subsequent reactions, under “oxo” conditions involving use of Rh4(CO)12 or Rh4(CO)12 in the presence of (R,R)-Diop (Diop = <2,2-dimethyl-1,3-dioxolane-4,5-diylbis (methylene)bis(diphenylphosphine)) as the catalyst precursor.The product first formed arises from formylation at the unsubstituted unsaturated carbon atom, and subsequently gives alpha-methyl-gamma-butyrolactone (1b), N,N-diethyl 2-methyl-4-hydroxy-butyramide (1e), and N, N-diethyl 1-methyl-3-(diethylamino)butyramide (1f).Hydrogenation of the substrate takes also place.The product distribution can be strongly influenced by the reactions conditions.For N,N,N',N'-tetraethyl itacondiamide (2) under similar reactions conditions only hydrogenation and isomerization products are formed. Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Electric Literature of 1679-47-6. In my other articles, you can also check out more blogs about 1679-47-6

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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An Asymmetric Nitroolefination of alpha-Alkyl-gamma-and delta-Lactones with Modified Nitroenamines

New chiral nitroenamines 4a,b having (S)-2-t-butyldimethylsiloxymethylpyrrolidine as an auxiliary were found to be very effective for asymmetric nitroolefination of alpha-alkyl-gamma- and delta-lactones.The enantiomeric excess of the product increased remarkably in the reaction with gamma-lactones compared with previous nitroenamines 1a,b.A possible chelation model for the transition state of the asymmetric nitroolefination is discussed.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Herbicidal 2-(aminophenyl)methyl derivatives of 3-isoxazolidinones or 3-oxazinones

Compounds of the formula, STR1 formulations thereof, and their use as herbicides are disclosed and exemplified.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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METHODS OF FORMING DIOL COMPOUNDS

Methods of forming a C4 to C7 diol compound, the methods including a first step of reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a C4 to C7 lactone; and a subsequent step of reacting the lactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure, wherein the second temperature is lower than the first temperature. Also disclosed are methods of forming a solvent, the methods including reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a solvent. Further disclosed herein are methods that include reacting mevalonolactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure to form a diol compound.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Characterization of organic matter from natural waters using tetramethylammonium hydroxide thermochemolysis GC-MS

The tetramethylammonium hydroxide (TMAH) thermochemolysis method was recently introduced for the qualitative characterization of organic matter from natural waters (NOM). Such characterizations were usually of a qualitative nature, and any semiquantitative assessments of individual compounds were often achieved by measuring relative areas and assuming unity as a response factor. In this paper we evaluate the quantitative measurement of many identified products characteristic of lignin and NOM using an internal standard approach. The relative standard deviation for most quantified compounds was between 1 and 10%. Four NOM samples, isolated by low-temperature, low-pressure evaporation and freeze-drying, were collected from temperate as well as tropical climates. Large variations were found between samples with respect to the distribution of compounds such as fatty acids, lignin-derived compounds, carbohydrate-derived compounds, and protein-derived compounds. We quantified most lignin-derived and aromatic TMAH products as well as fatty acids (as their methyl esters, FAME) that were found in this set of NOM samples. The contribution of lignin-derived compounds to the total quantified TMAH product distribution in these four samples varied between 21 and 35%. The contribution of FAMEs ranged from 32 to 51% whereas the contribution from non-lignin aromatic compounds was 24-32%. TMAH thermochemolysis potentially provides significant information about NOM sources, compared with other degradative techniques, since both lignin-derived compounds and lipids can be quantitatively and simultaneously investigated.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem