- Synthetic method 4 - alkoxyphenol compounds
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The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.
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Paragraph 0046-0048
(2021/09/29)
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- Para -Selective hydroxylation of alkyl aryl ethers
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para-Selective hydroxylation of alkyl aryl ethers is established, which proceeds with a ruthenium(ii) catalyst, hypervalent iodine(iii) and trifluoroacetic anhydride via a radical mechanism. This protocol tolerates a wide scope of substrates and provides a facile and efficient method for preparing clinical drugs monobenzone and pramocaine on a gram scale.
- Zhu, Runqing,Sun, Qianqian,Li, Jing,Li, Luohao,Gao, Qinghe,Wang, Yakun,Fang, Lizhen
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supporting information
p. 13190 - 13193
(2021/12/16)
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- Nano-NiFe2O4 as an efficient catalyst for regio- and chemoselective transfer hydrogenation of olefins/alkynes and dehydrogenation of alcohols under Pd-/Ru-free conditions
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Here, we have demonstrated the magnetic nano-NiFe2O4 catalyzed transfer hydrogenation of olefins/alkynes using isopropyl alcohol as a source of hydrogen under ligand/base/Pd-/Ru-metal-free conditions, and dehydrogenation of alcohols under oxidant-free conditions.
- Payra, Soumen,Saha, Arijit,Banerjee, Subhash
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p. 52495 - 52499
(2016/06/13)
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- Facile conversion of para-benzoquinones to para-alkoxyphenols with primary/secondary alcohols and amberlyst-15: A process showing novel reducing property of such alcohols
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A new efficient methodology has been developed for the synthesis of para-alkoxyphenols, an important group of anti-melanoma compounds, by heating alcoholic solutions of para-benzoquinones in the presence of amberlyst-15. The most notable feature here is the behaviour of the used primary or secondary alcohol as an effective reducing agent.
- Mondal, Rina,Guha, Chayan,Mallik, Asok K.
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supporting information
p. 86 - 89
(2014/01/06)
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- A convenient approach for the deprotection and scavenging of the PMB group using POCl3
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A convenient and high yielding approach for the deprotection and scavenging of the p-methoxybenzyl (PMB) group in PMB ethers and PMB esters was developed using POCl3 as the reagent. 4-Methoxybenzyl chloride, a starting material used for the preparation of PMB ethers and esters was regenerated in the deprotection step. This mild and selective procedure tolerates several acid sensitive functional groups. The Royal Society of Chemistry 2013.
- Ilangovan, Andivelu,Saravanakumar, Shanmugasundar,Malayappasamy, Subramani,Manickam, Govindaswamy
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p. 14814 - 14828
(2013/09/02)
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- Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, trichoplusia ni: Potential insect behavior control agents
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The antifeedant, oviposition deterrent, and toxic effects of individual dialkoxybenzene compounds/sets and of hydroxy- or alkoxy-substituted allylbenzenes, obtained through Claisen rearrangement of substituted allyloxybenzenes, were assessed against the cabbage looper, Trichoplusia ni, in laboratory bioassays. Most of the compounds/sets strongly deterred larval feeding, with some exhibiting mild toxic and oviposition deterrent effects as well. Some of the compounds/sets were more active than the commercial insect repellent, DEET (N,N-diethyl-m-toluamide), as both feeding and oviposition deterrents against the cabbage looper. On the basis of the obtained oviposition data a general hypothesis was proposed regarding the oviposition sites: one binding mode with the alkyl and allyl groups on the same side of the benzene ring resulted in deterrence, the other with alkyl and allyl groups on opposite sides of the benzene ring resulted in stimulation. The results suggest some structure-activity relationships useful in improving the efficacy of the compounds and designing new, nontoxic insect control agents for agriculture.
- Akhtar, Yasmin,Yu, Yang,Isman, Murray B.,Plettner, Erika
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scheme or table
p. 4983 - 4991
(2011/08/06)
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- Screening of dialkoxybenzenes and disubstituted cyclopentene derivatives against the cabbage looper, Trichoplusia ni, for the discovery of new feeding and oviposition deterrents
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The antifeedant, oviposition deterrent, and toxic effects of dialkoxybenzene minilibraries and of disubstituted cyclopentene minilibraries (i.e., consisting of four to five compounds) along with their pure constituent compounds were assessed against third instar larvae and adults of the cabbage looper, Trichoplusia ni, in laboratory bioassays in a search for new insect control agents. These compounds mimic naturally occurring bioactive odorants and tastants and are relatively easily prepared from commodity chemicals. Most of these libraries strongly deterred larval feeding, with some exhibiting strong toxic and oviposition deterrent effects as well. Our results suggest some structure-function relationships within these libraries. Replacement of a methyl group with larger alkyl substituents increased the feeding deterrent effects in most cases. The presence of a free hydroxyl group, irrespective of the carbon framework or alkyl substituent, served to reduce feeding deterrent effects in all series of compounds. Further, exceeding a certain group size also generally had a detrimental effect. This information will be useful in designing new insect control agents for agriculture. Some of these libraries and compounds may have potential for development as commercial insecticides.
- Akhtar, Yasmin,Isman, Murray B.,Paduraru, Peggy M.,Nagabandi, Srinivas,Nair, Ranjeet,Plettner, Erika
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scheme or table
p. 10323 - 10330
(2009/10/02)
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- Palladium charcoal-catalyzed deprotection of O-allylphenols
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Allyl aryl ethers can be easily cleaved by the use of 10% Pd/C under mild and basic conditions. The present reaction would involve a SET process rather than a π-allyl-palladium complex. The scope and limitation of this new deprotective methodology is also described.
- Ishizaki, Miyuki,Yamada, Makoto,Watanabe, Shin-Ichi,Hoshino, Osamu,Nishitani, Kiyoshi,Hayashida, Maiko,Tanaka, Atsuko,Hara, Hiroshi
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p. 7973 - 7981
(2007/10/03)
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- One-pot synthesis of phenols from aromatic aldehydes by Baeyer-Villiger oxidation with H2O2 using water-tolerant Lewis acids in molecular sieves
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The heterogeneous oxidation systems Sn-Beta/H2O2 and Al-Beta/H2O2 were both active for the Baeyer-Villiger oxidation of aromatic aldehydes. With alkoxy substituents in ortho and especially in para position, the corresponding formate ester was the primary reaction product with excellent selectivity. The highest selectivity toward the ester was obtained with the Sn-Beta catalyst in dioxane as solvent. High selectivities of the corresponding phenol could be obtained by employing ethanol or aqueous acetonitrile as solvent with Sn-Beta. Al-Beta was more efficient as catalyst for both Baeyer-Villiger oxidation and ester hydrolysis and, thus achieved high yields for the corresponding alcohol. However, this was a less selective catalyst than Sn-Beta zeolite. Sn-Beta was a chemoselective catalyst when the aldehyde reactant contained olefinic groups in an alkyl chain. With these reactants, the Al-zeolite gave no activity. Other classical BV oxidants, e.g., peracids, also yielded the epoxidation products. Thus, Sn-Beta catalysts open a new entry to aromatic phenols with unsaturated alkyl substituents that are interesting intermediates in the chemical industry.
- Corma, Avelino,Fornes, Vicente,Iborra, Sara,Mifsud, Maria,Renz, Michael
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- ALDEHYDE CONVERSION METHOD USING A MOLECULAR SIEVE AND THE USE OF THE MOLECULAR SIEVE AS A CATALYST IN SAID METHOD
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The inversion relates to an aldehyde conversion method comprising putting an aldehyde into contact with oxygenated water and with a catalyst, under oxidation conditions, wherein the catalyst is a molecular sieve with pores of a diameter of at least 0.52 nm and has an empirical formula in a calcined and dehydrated form of(SnxTiySi1-x-y-zGez) O2 wherein x is a molar fraction of the tin and has a value between 0.001 and 0.1; y is a molar fraction of titanium and has a value from zero to 0.1; and z is the molar fraction molar of the germanium and has a value from zero to 0.08.
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- β1- and β2-adrenoceptor antagonist activity of a series of para- substituted N-isopropylphenoxypropanolamines
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To further explore the structure-activity relationships of β- adrenoceptor (β-AR) antagonists, a series of 25 para-substituted N- isopropylphenoxy-propanolamines were synthesised, nine of which are new compounds. All have been examined for their ability to antagonise β1-ARs in rat atria and β2-ARs in rat trachea. Substitution in the para-position of the phenyl ring is thought to confer β3-specificity and the selectivity of these compounds for the β1-AR ranges from 1.5-234. None of the compounds tested were selective for the β2-AR. Of the 25 compounds studied, 22 had reasonable (pA2 > 7) potencies for the rat β1-AR. Only compound 1 displayed reasonable (pA2 > 7) potency for the rat β2-AR. Twenty two compounds were used as the training set for comparative molecular field analysis (CoMFA) of antagonist potency (pA2) at the rat β1- and β2-ARs. The inclusion of a number of additional physical characteristics improved the QSAR analysis over models derived solely using the CoMFA electrostatic and steric fields. The final models predicted the β1- and β2-AR potency of the compounds in the training set with high accuracy (r2 = 0.93 and 0.86 respectively). The final β1-AR model predicted the β1-potencies of two out of the three test compounds, not included in the training set, with residual PA2 values 2-AR model (residual pA2 values -0.38).
- Louis, Simon N.,Nero, Tracy L.,Iakovidis, Dimitri,Colagrande, Felicia M.,Jackman, Graham P.,Louis, William J.
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p. 919 - 937
(2007/10/03)
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- O-MONOALKYLATION OF HYDROQUINONE BY ALCOHOLS
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The dependence of the initial rate of O-monoalkylation of hydroquinone by alcohols on the F constant of the alcohol radical has the following form: w0*104 = 21(F + 1.28)-5 + 0.44.The previously unknown steric constants F for hexyl, heptyl, cyclohexyl, and 2-ethoxyethyl radicals were determined by means of this relationship.
- Rybin, A. G.,Orlov, A. V.,Zil'berman, E. N.,Barskova, M. Z.
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p. 1609 - 1611
(2007/10/02)
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- REACTION OF MONOSUBSTITUTED AROMATIC HYDROCARBONS WITH STYRENE
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1,1-Phenylarylethanes were obtained by the reaction of styrene with some monosubstituted aromatic hydrocarbons in the presence of titanium tetrachloride.It was established that electron-donating substituents have an effect on the yield of the arylalkylation products.
- Grushin, A. I.,Grigor'ev, V. V.,Prokof'ev, K. V.,Kozlova, N. M.
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p. 1991 - 1993
(2007/10/02)
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- LIQUID CRYSTALLINE PROPERTIES OF 4-N-ALKOXYPHENYL 4-NITROBENZOATES.
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Twelve 4-alkoxyphenyl esters of 4-nitrobenzoic acid were synthesized. The mesophases were identified and the transition temperatures and enthalpies determined. The above series shows considerable similarity to the reverse analogues, i. e. , the 4-nitro-phenyl 4-n-alkoxybenzoates.
- Galewski,Sobczyk
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