83-40-9Relevant articles and documents
Synthesis of cresotic acids by carboxylation of cresols with sodium ethyl carbonate
Suerbaev, Kh. A.,Chepaikin,Kudaibergenov, N. Zh.,Zhaksylykova, G. Zh.
, p. 646 - 650 (2016/08/16)
Carboxylation of o-cresol, m-cresol, and p-cresol with sodium ethyl carbonate (SEC) proceeds regioselectively with the formation of cresotic acids: 2-hydroxy-3-methylbenzoic acid, 2-hydroxy-4-methylbenzoic acid, and 2-hydroxy-5-methylbenzoic acid, respectively. Optimal conditions for conducting the process have been found to be as follows: the reactants ratio of [cresol]: [sodium ethyl carbonate] = (1.5–2): 1, T = 180–185°C, PCO2 = 10 atm, and t = 6–7 h. Simple and convenient methods for the synthesis of cresotic acids, which can be used for their industrial manufacturing, have been developed.
Carboxylation of Phenols with CO2 at Atmospheric Pressure
Luo, Junfei,Preciado, Sara,Xie, Pan,Larrosa, Igor
supporting information, p. 6798 - 6802 (2016/05/11)
A convenient and efficient method for the ortho-carboxylation of phenols under atmospheric CO2 pressure has been developed. This method provides an alternative to the previously reported Kolbe-Schmitt method, which requires very high pressures of CO2. The addition of a trisubstituted phenol has proved essential for the successful carboxylation of phenols with CO2 at standard atmospheric pressure, allowing the efficient preparation of a broad variety of salicylic acids.
General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation
Wang, Yang,Gevorgyan, Vladimir
, p. 2255 - 2259 (2015/02/19)
A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.
Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction
Wuensch, Christiane,Gross, Johannes,Steinkellner, Georg,Lyskowski, Andrzej,Gruber, Karl,Glueck, Silvia M.,Faber, Kurt
, p. 9673 - 9679 (2014/03/21)
The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense of bicarbonate as CO2 source is reported. In contrast to the classic Kolbe-Schmitt reaction, the biocatalytic equivalent proceeded in a highly regioselective fashion exclusively at the ortho-position of the phenolic directing group in up to 80% conversion. Several enzymes were identified, which displayed a remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino- functionalities. Based on the crystal structure and molecular docking simulations, a mechanistic proposal for 2,6-dihydroxybenzoic acid decarboxylase is presented.
Preparation and X-ray structural study of 1-arylbenziodoxolones
Yusubov, Mekhman S.,Yusubova, Roza Y.,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 3767 - 3773 (2013/06/05)
Various 1-arylbenziodoxolones can be conveniently prepared from 2-iodobenzoic acid and arenes by a one-pot procedure using Oxone (2KHSO 5·KHSO4·K2SO4) as an inexpensive and environmentally safe oxidant. This procedure is also applicable for the synthesis of the 7-methylbenziodoxolone ring system using 2-iodo-3-methylbenzoic acid as starting compound. Structures of four 1-arylbenziodoxolone derivatives were established by single-crystal X-ray diffraction analysis. An enhanced reactivity of 1-aryl-7-methylbenziodoxolones toward nucleophiles compared to unsubstituted 1-arylbenziodoxolones has been found.
Iron-promoted ortho-And/or ipso-hydroxylation of benzoic acids with H 2O2
Makhlynets, Olga V.,Das, Parthapratim,Taktak, Sonia,Flook, Margaret,Mas-Balleste, Ruben,Rybak-Akimova, Elena V.,Que Jr., Lawrence
experimental part, p. 13171 - 13180 (2010/07/03)
Regioselective hydroxylation of aromatic acids with hydrogen peroxide proceeds readily in the presence of iron(II) complexes with tetradentate aminopyridine ligands [FeII(BPMEN)-(CH3CN) 2](ClO4)2 (1) and [FeII(TPA)- (CH3CN)2](OTf)2 (2), where BPMEN=N, N'-dimethyl-N, N'-bis(2-pyridylmethyl)-1,2-ethylenediamine, TPA=tris-(2- pyridylmethyl)amine. Two cis-sites, which are occupied by labile acetonitrile molecules in 1 and 2, are available for coordination of H2O 2 and substituted benzoic acids. The hydroxylation of the aromatic ring occurs exclusively in the vicinity of the anchoring carboxylate functional group: ortho-hydroxylation affords salicylates, whereas ipso-hydroxylation with concomitant decarboxylation yields phenolates. The outcome of the substituent directed hydroxylation depends on the electronic properties and the position of substituents in the molecules of substrates:3-substituted benzoic acids are preferentially ortho-hydroxylated, whereas 2-and, to a lesser extent, 4-substituted substrates tend to undergo ipso-hydroxylation/decarboxylation. These two pathways are not mutually exclusive and likely proceed via a common intermediate. Electron-withdrawing substituents on the aromatic ring of the carboxylic acids disfavor hydroxylation, indicating an electrophilic nature for the active oxidant. Complexes 1 and 2 exhibit similar reactivity patterns, but 1 generates a more powerful oxidant than 2. Spectroscopic and labeling studies exclude acylperoxoiron(III) and FeIV=O species as potential reaction intermediates, but strongly indicate the involvement of an FeIII-OOH intermediate that undergoes intramolecular acid-promoted heterolytic O-O bond cleavage, producing a transient iron(V) oxidant.
INHIBITORS OF STEAROYL-COA DESATURASE
-
, (2009/06/27)
Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.
PROCESS FOR PRODUCTION OF HYDROXYBENZOIC ACIDS
-
Page/Page column 8, (2010/02/14)
The present invention provides A method for producing a hydroxybenzoic acid compound comprising, preparing an alkali metal salt of a phenol compound from the phenol compound, and reacting the alkali metal salt of the phenol compound with carbon dioxide, wherein the step of preparing the alkali metal salt of the phenol compound from the phenol compound comprises the steps of:a) reacting an alkali metal alkoxide with an excess amount of the phenol compound, which is in excess of the alkali metal alkoxide, to give the alkali metal salt of the phenol compound, andb) distilling away the generated alcohol from the reaction simultaneously with carrying out step a). The method of the present invention makes it possible to produce hydroxybenzoic acid compound in high yield without using aprotic polar organic solvent.
Chromone fungicides
-
, (2008/06/13)
Compounds of the formula where one of Z and Y is CO and the other is C-W-R2 and the dotted line indicates a double bond is present where necessary to meet valency requirements, W is O, S(O)n, N(R3), N(R3)(R4), N(R3)O or ON(R3); R1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or heterocyclyl group; R2, R3 and R4, which may be the same or different, are as defined above for R1, or are acyl, or R2 and R3 or R2 and R4 or R3 and R4 together with the nitrogen or oxygen to which they are attached form an optionally substituted ring which may contain other hetero atoms; each X, which may be the same as or different from any other X, is halogen, CN, NO2, SF5, B(OH)2, triakylsilyl or a group E, OE or S(O)nE where E is a group as defined hereinbefore for R2 or is optionally substituted amino; or two adjacent groups X together with the atoms to which they are attached form an optionally substituted carbocyclic or heterocyclic ring; n is 0, 1 or 2; and p is 0 to 4 have fungicidal activity. Many of the compounds are novel.
External preparation for skin
-
, (2008/06/13)
An external preparing for skin comprising one or more than two types of 2-hydroxy benzoic acid derivative and/or salt thereof represented by the following formula: STR1 wherein R is an alkoxy group or alkyl group in the formula. The external preparation for the skin according to the present invention has a suppression effect on melanine generation by inhibition of tyrosinase activity. Accordingly, an excellent bleaching effect based upon the suppression of chromatosis and a high degree of safety can be obtained.
