1703-52-2Relevant academic research and scientific papers
METAL CATALYST AND HYDROGEN GAS FREE APPROACHES FOR SELECTIVE REDUCTION OF ALDEHYDE TO METHYL GROUP OF DIFFERENT SUBSTITUTED FURANS
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Page/Page column 18-19, (2021/08/27)
The present invention relates to 5-methyl substituted furan compounds of general formula (I) and process for the preparation thereof: OR1R2 R3CH3(I) Particularly, the present invention relates to a metal catalyst and hydrogen gas free, atom-economy, highly selective and low-cost process for the preparation of methyl substituted furan compounds from different aldehyde substituted furan compounds.
Synthesis method of 2,5-furandicarboxylic acid
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, (2020/06/09)
The invention discloses a synthesis method of 2,5-furandicarboxylic acid. The synthesis method comprises the following steps: 1, hydrogenation of furfural into methyl furan; 2, acetylation of methyl furan; 3, hydrogenation of 5-methyl-2-acetylfuran; and 4, oxidation of 2-methyl-5-ethylfuran. According to the invention, a green renewable bio-based platform compound furfural is used as a raw material; and compared with a process for preparing 2,5-furandicarboxylic acid by using 5-hydroxymethylfurfural as a raw material, the method disclosed by the invention has the advantages that the source ofthe used raw material is wider, the raw material is easy to produce, productivity is higher, the cost of the raw material is lower, the cost of a used oxidation catalyst is low, and large-scale production is facilitated. Compared with a noble metal complex catalyst used in a process adopting CO carbonylation for carbon chain growth, a carbon chain growth strategy catalyst used in the invention issolid acid, so cost is greatly reduced.
Production of p-Methylstyrene and p-Divinylbenzene from Furanic Compounds
Koehle, Maura,Sara?i, Erisa,Dauenhauer, Paul,Lobo, Raul F.
, p. 91 - 98 (2017/01/17)
A four-step catalytic process was developed to produce p-methylstyrene from methylfuran, a biomass-derived species. First, methylfuran was acylated over zeolite H-Beta with acetic anhydride. Second, the acetyl group was reduced to an ethyl group with hydrogen over copper chromite. Third, p-ethyltoluene was formed through Diels–Alder cycloaddition and dehydration of 2-ethyl-5-methyl-furan with ethylene over zeolite H-Beta. Dehydrogenation of p-ethyltoluene to yield p-methylstyrene completes the synthesis but was not investigated because it is a known process. The first two steps were accomplished in high yield (>88 %) and the Diels–Alder step resulted in a 67 % yield of p-ethyltoluene with a 99.5 % selectivity to the para isomer (final yield of 53.5 %). The methodology was also used for the preparation of p-divinylbenzene. It is shown that acylation of furans over H-Beta zeolites is a highly selective and high-yield reaction that could be used to produce other valuable molecules from biomass-derived furans.
Methyl Hydrazinocarboxylate as a Practical Alternative to Hydrazine in the Wolff-Kishner Reaction
Cranwell, Philippa B.,Russell, Andrew T.,Smith, Christopher D.
supporting information, p. 131 - 135 (2015/12/26)
Herein we describe a facile protocol for the reduction of aromatic ketones and aldehydes to the corresponding methylene unit. The procedure involves isolation of a carbomethoxyhydrazone intermediate that is easily decomposed to the reduced product without the requirement for large quantities of pernicious hydrazine.
Laccase-catalyzed stereoselective oxidative ring opening of 2,5-dialkylfurans into 2-ene-1,4-diones using air as an oxidant
Asta, Chimene,Conrad, Juergen,Mika, Sabine,Beifuss, Uwe
supporting information; experimental part, p. 3066 - 3069 (2011/12/21)
The laccase-catalyzed ring opening of 2,5-dimethylfuran using air as an oxidant stereoselectively yields (Z)- or (E)-3-hexene-2,5-dione depending on the mediator employed: with TEMPO the (Z)-3-hexene-2,5-dione is formed, while a combination of TEMPO and violuric acid gives (E)-3-hexene-2,5-dione. The (Z)-selective ring cleavage was extended to a variety of symmetrical and unsymmetrical 2,5-dialkylfurans. The Royal Society of Chemistry.
Reactions of Some Cyclic Ethers in Superacids
Baig, Mirza Azam,Banthorpe, Derek V.,Carr, Graham,Whittaker, David
, p. 1981 - 1986 (2007/10/02)
The reactions of some epoxides and tetrahydrofuran derivatives in superacidic media have been studied.The tetrahydrofurans decompose only at 0 deg C or above, yielding, in some cases, unsaturated carbocations which react to give carbocyclic products, though many yield only tar.Cyclohexene oxides decompose more readily; unsubstituted, they slowly form an allylic ion; with one carbon at the epoxide link substituted they yield the ketone, and with both carbons substituted they give the ring-contracted aldehyde.Limonene 1,2-oxide behaves in a similar manner, though yielding small amounts of the ring-contracted protonated aldehyde (10).Reaction of geraniol 2,3-oxide is initially similar but the intermediate is intercepted intramolecularly to yield the hydroxy-iridoid ethers, 3,3,6β-trimethyl-cis-perhydrocyclopentafuran and 3,3,6α-trimethyl-cis-perhydrocyclopentafuran.Protonation of cyclohexene oxide or norbornene oxide yields onium salts, stable at -70 deg C, which show the addition to be either unsymmetrical (i.e. edge protonation) or to take place in two different positions.
Stereoselective Syntheses of Alcohols, XXVI. - Synthesis of 3-Methyl-2,6-dideoxyhexoses by Addition of an Allenyltitanium Reagent to Aldehydes.
Hoffmann, Reinhard W.,Lanz, Joachim W.,Metternich, Rainer
, p. 161 - 166 (2007/10/02)
In contrast to the nonregioselective addition of 3-methoxy-3-methylallenyllithium (8) to aldehydes the corresponding titanium reagent 14 produced only propargylic type adducts.The products resulting on addition of 14 to L-2-(benzyloxy)propionaldehyde have been converted into 3-O-methyl-3-methyl-2,6-dideoxyhexoses 23 and 25 of arabino and xylo configuration.
Synthesis of Biheteroaromatic Compounds via the Isoxazoline Route
Ghabrial, Sami S.,Thomsen, I.,Torssell, K. B. G.
, p. 426 - 434 (2007/10/02)
A number of heteroaromatically substituted furans, thiophenes, pyrroles, pyridines and benzenes have been prepared via the 2-isoxazoline route.N-Acetylnornicotyrine is prepared from N-allylacetamide and 3-pyridinecarboxaldoxime.
