cas 118-82-1, 4,4'-Methylenebis(2,6-di-tert-butylphenol)

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Practical process for the air oxidation of cresols: Part A. Mechanistic investigations
The catalytic air oxidation of p-cresol and 2,6-di-tert-butyl-4- methylphenol to the corresponding benzaldehydes was investigated to determine the mechanism at work in these oxidation reactions. A number of intermediates and byproducts, mainly in the form of dimers, were observed during the course of the reactions, and their structures were elucidated by spectroscopic and chromatographic methods. The existence of these compounds in the reaction mixtures, and their proposed methods of formation, provided further insight into the mechanism involved in these oxidations.
Barton, Benita,Logie, Catherine G.,Schoonees, Barbara M.,Zeelie, Bernard
p. 62 - 69
(2005)
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Synthesis of unsymmetrical hydroxybenzylphenols from 2-isobornyl-4-methylphenol
2-Hydroxymethyl-6-isobornyl-4-methylphenol was synthesized from 2-isobornyl-4-methylphenol. Reactions of this hydroxymethyl derivative with 2,4- and 2,4-di-tert-butylphenols gave new unsymmetrical hydroxybenzylphenols.
Buravlev,Chukicheva, I. Yu.,Elfimova,Suponitskii, K. Yu.,Kutchin
p. 623 - 628
(2015)
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Thermal decomposition of 2,6-di-tert-butyl-4-dimethylaminomethylphenol
Products of thermolysis of 2,6-di-tert-butyl-4-dimethylaminomethylphenol were determined qualitatively and quantitatively by GLC, UV, and 1H NMR methods. The kinetics of the reaction was studied. The thermolysis products were studied as the inhibitors in thermopolymerization of monomers.
Zakharova,Khismatullina,Ivanov
p. 1787 - 1789
(1997)
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Phenolic compound as well as preparation method and application thereof
The invention provides a phenolic compound as well as a preparation method and application thereof. The structure of the phenolic compound is shown as a general formula (I), R1 and R1'can be the sameor different and are independently selected from CnH(2n+m), n is an integer ranging from 3 to 30, m is 1, -1, -3 or -5, R2 and R2' can be the same or different and are independently selected from C1-C8 straight chain or branched chain alkyl respectively; and R3 is selected from C1-C6 straight chain or branched chain alkylene. The phenolic compound provided by the invention has very excellent oxidation resistance, and can be used as an antioxidant in lubricating oil, lubricating grease, fuel oil, plastic and rubber. The preparation method disclosed by the invention is simple and feasible, and the yield and product purity are relatively high.
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Paragraph 0056-0057

(2020/05/05)

Phenolic derivative as well as preparation method and application thereof
The invention provides a phenol derivative as well as a preparation method and application thereof. The structure of the phenolic derivative is shown as a formula (I), wherein the definition of each group is shown in the specification. The phenolic derivative can be used as an antioxidant in lubricating oil, lubricating grease, plastics and rubber, and can also be used as base oil of lubricating oil and lubricating grease, and an anti-wear agent of lubricating oil and lubricating grease. The phenolic derivative disclosed by the invention has excellent oxidation resistance, lubricating property, antifriction property, viscosity-temperature property and low-temperature property.
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Paragraph 0496-0497

(2020/05/05)

Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C[sbnd]C ipso-substitution reaction using proton-exchanged montmorillonite as media
We present here proton-exchanged montmorillonite-mediated an unusual transformation of 4-hydroxy and 4-methoxybenzylic alcohols to form symmetrical benzylic ethers and diarylmethanes under mild conditions. Nuclear magnetic resonance spectroscopy and density functional theory calculations support a plausible mechanism, which includes a distinctive aromatic C[sbnd]C ipso-substitution reaction with a hydroxymethyl group as the C-based leaving group.
Chen, Dongyin,Chen, Xuan,Dong, Zezhong,Jiang, Nan,Li, Fei,Yun, Yangfang,Zhou, Yu
supporting information

(2020/11/12)

Antioxidant 1425 production process
Antioxidant 1425 is an important chemical industry product. The basic process comprises a benzylation reaction, an alkaline hydrolysis reaction, and a complexing reaction. The production process comprises: pouring distillation kettle residue loaded into a barrel into a 2000 L enamel reaction kettle, maintaining a certain temperature (95-100 DEG C), slowly adding a prepared 2-5% sodium hydroxide solution according to a ratio of 1:1.1 under stirring, stirring for 2 h, carrying out standing layering, neutralizing the lower layer water phase, transferring into an antioxidant 1425 complexing kettle, mixing with the hydrolyzate in the production, extracting with solvent oil, recovering the small amount of the antioxidant 1425, and carrying out drying crystallization on the upper layer organic phase to obtain the product antioxidant 4426 product, wherein the main components of the dried waste gas are water vapor and a small amount of non-methane total hydrocarbons, and are subjected to unorganized emission.
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Paragraph 0001

(2017/07/20)

Iridium-Catalyzed C4-Alkylation of 2,6-Di-tert-butylphenol by Using Hydrogen-Borrowing Catalysis
An iridium-catalyzed hydrogen-borrowing process has been developed whereby 2,6-di-tert-butylphenol can be alkylated at the C4-position by using a range of primary alcohols (11 examples, 40-93% yield). Following this, a selection of the products obtained underwent retro-Friedel-Crafts reactions to provide para-substituted phenols, which could potentially undergo further synthetic manipulations.
Frost, James R.,Cheong, Choon Boon,Donohoe, Timothy J.
p. 910 - 916
(2017/02/15)

Based on mixed alkali catalyst catalytic double-phenolic antioxidant preparation method and application (by machine translation)
The invention discloses a mixed alkali catalyst based on double-phenol method for preparing an antioxidant and application. The preparation method comprises: the two alkyl substituted phenol and aldehyde compound is placed in the closed and in the reactor and in a mixed alkali catalyst can choose to add or not to add the presence of an organic solvent of the reaction is carried out under the condition of, and in the after the reaction is finished after processing the obtained compound antioxidant product double phenol apperception, the anti-oxidant product can be used for preparing the lubricating oil composition, composition or burns the oil line as plastic, rubber, such as anti-aging agent. Antioxidant bisphenol compounds of this invention for the production of simple operation, mild conditions, such as the sources of raw materials and catalyst of extensive and is cheap and easy to obtain, the reaction cycle is short, it is easy to control, process with high safety, low energy consumption in the producing process, the yield of the product and high purity, and can effectively control and reducing pollutant emissions, is a safe and energy-saving, environmental protection art. (by machine translation)
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Paragraph 0056; 0057

(2017/03/08)

Preparation method for hindered bisphenol type antioxidant
The invention relates to a preparation method for a hindered bisphenol type antioxidant. The preparation method comprises the following process steps: adding 2,6-ditert-butyl phenol and a catalyst into a reaction vessel, wherein per 1 mol of 2,6-ditert-butyl phenol is added with 3 to 8 mL of the catalyst; carrying out stirring under the temperature condition of 40 to 60 DEG C until the mixture is melted; adding a formaldehyde solution, wherein a mol ratio of formaldehyde and 2,6-ditert-butyl phenol is 1: (2.0-2.2); after the completion of addition, carrying out heating to 60 to 80 DEG C, carrying out reaction for 2 to 5 hours, then carrying out pumping filtration, and carrying out washing by using warm water with a temperature of 40 to 50 DEG C; subjecting an obtained filter cake to vacuum drying, and recrystallizing an obtained crude product, wherein per 1 g of the crude product is added with 0.5 to 5 mL of a recrystallization solvent; and carrying out vacuum drying so as to obtain a yellow needle-like crystal. The method provided by the invention does not need adding alcohol organic solvents in the preparation process, has the advantages of simple production process, low cost, few by-products in a preparation process, and high antioxidant purity and yield, and is beneficial for environmental protection.
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Paragraph 0067; 0068

(2016/12/01)

METHODS AND COMPOSITIONS FOR INHIBITING VINYL AROMATIC MONOMER POLYMERIZATION
Methods and compositions are provided for inhibiting the polymerization of a vinyl aromatic monomer, such as styrene monomer, during elevated temperature processing thereof or during storage or shipment of polymer containing product. The compositions comprise a combination of a quinone methide derivative A) and a phenol compound B). The methods comprise adding from about 1-10,000 ppm of the combination to the monomer containing medium, per one million parts of the monomer.
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(2013/03/26)

Convenient synthesis of 2,2-and 4,4-methylenebisphenols with bulky alkyl substituents and evaluation of their antioxidant activity
The work is devoted to a convenient procedure of the synthesis of 2,2-and 4,4-methylenebisphenols with alkyl substituents in heterogeneous catalysis. This compounds were obtained with yields up to 87% by reflux of 2,4-or 2,6-dialkylphenols with HCHO in n-octane in the presence of KSF clay. We found that the antioxidant activity on DPPH test for two novel methylenebisphenols having isobornyl fragments was comparable with control drugs.
Buravlev, Evgeny V.,Chukicheva, Irina Yu.,Borisenkov, Mikhail F.,Kutchin, Aleksandr V.
p. 3670 - 3676,7
(2020/08/31)

GREEN AND ATOM-ECONOMICAL PROCESSES FOR PRODUCING PHENOLIC ANTIOXIDANTS
Processes for producing 1,3,5-trimethyI-2,4,6-tris(3,5-dialkyl-4- hydroxybenzyl)benzene are provided, in particular such processes that utilize 2,6-di-tert- butylphenol, paraformaldehyde, a secondary amine, mesitylene, and acetic acid.
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Page/Page column 9-10

(2011/02/24)

MULTI-RING ANTIOXIDANTS WITH ANTIWEAR PROPERTIES
Described are multi-ring antioxidant products comprising at least one sulfur- bridged aromatic hydrocarbon compound substituted on at least one of its aromatic rings by at least one sterically hindered 3,5-dihydrocarbyl-4-hydroxybenzyl moiety. Such products have the formula : R-Sn-R[-S-R]m wherein each R is, independently, an aromatic hydrocarbon group having 6-12 carbon atoms, wherein m is 0-20, wherein n is 1-6 when m is 0, and when n is 1, m is 1-20; and wherein at least one of R, R1, and R2 is substituted by at least one such sterically hindered moiety. The preparation of such products and their use as antioxidants in compositions normally susceptible to oxidative degradation in oxygen or air, e.g., liquid fuel and lubricants, are also described.
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Page/Page column 17

(2010/04/03)

Development of a one-stage synthesis of 2,6-di-tert-4-ethylbutylphenol from 2,6-di-tert-butylphenol
Investigation of the catalyzed reaction of 2,6-di-tert-butylphenol with ethanol, ethylene glycol, oligomeric glycols, and paraldehyde in a strongly basic medium permitted to develop a technologically suitable procedure for manufacture of 2,6-di-tert-4-ethyl-butylphenol, used in the synthesis of Antioxidant-425.
Krysin,Pokrovskii
experimental part
p. 1728 - 1733
(2009/02/06)

PROCESSES SUITABLE FOR PRODUCING MACROMOLECULAR ANTIOXIDANT COMPOSITIONS
This invention relates to processes for the production of reaction mixtures, which find use as antioxidants in a variety of applications, using sterically hindered 4-hydroxymethyl-2,6-dihydrocarbylphenol and aromatic amines or heterocyclic compounds. Formula (I).
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Page/Page column 18-20

(2008/12/05)

4-Formyl amino-n-methylpiperidine derivatives, the use thereof as stabilisers and organic material stabilised therewith
The present invention relates to 4-formylamino-N-methylpiperidine derivatives of the formula (I) where the variables are as defined in the Description, to a process for preparing these piperidine derivatives, to the use of these piperidine derivatives of the invention, or prepared according to the invention, for stabilizing organic material, in particular for stabilizing plastics or coating materials, and also to the use of these piperidine derivatives of the invention, or prepared according to the invention, as light stabilizers or stabilizers for wood surfaces. The present invention further relates to stabilized organic material which comprises these piperidine derivatives of the invention or prepared according to the invention.
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(2008/06/13)

Attempted Synthesis of a Stable, Quintet, Tetraphenoxyl Tetraradical: Facile Rearrangement of a Substituted Bicyclobutane
The preparation of tetraphenol 3 and its attempted oxidation to tetraradical 2 are described. Tetraphenoxyl 2 was envisioned as a more stable analog of the previously reported, quintet tetraradical 1. However, EPR studies on 3 and model compounds and crystallographic characterization of the product from oxidation of 3 suggest that 2 is not a viable target. Apparently, 2 or an intermediate in the multistep oxidation path leading to it undergoes a ring closure to a bicyclobutane. The bicyclobutane, in turn, undergoes a surprisingly facile rearrangement to the analogous butadiene structure.
Anderson, Kraig K.,Shultz, David A.,Dougherty, Dennis A.
p. 7575 - 7584
(2007/10/03)

Lubricant composition
A composition comprising a) a lubricant or a hydraulic fluid and b) at least one compound of the general formula I STR1 in which x=1 or 2 and, if x=1, R is as defined for R1 or R3 --O-- or, if x=2, R is as defined for R8, and R1 and R3 are, for example, alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, or alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3, or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR2 or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3 and interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR3 and R2 is NR4 R5, --OR6 or --SR7, and R4 and R5 are identical or different and are, for example, --H, alkyl, phenyl, naphthyl, aralkyl or alkaryl, or R4 and R5, together with the N atom linking them, form, for example, a piperidine or morpholine radical, and R6 and R7 can be alkyl which may be interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR4 or are, for example, phenyl, naphthyl, alkaryl or aralkyl, and R8 can be alkylene which may be interrupted by at least one --O-- group or alkylidene which may be interrupted by at least one --O-- group. Some of the compounds of the formula I are novel. The compositions show an improved stability towards oxidative degradation, confer protection under extreme pressures and reduce frictional wear.
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(2008/06/13)

New approach to p-hydroxybenzylation of arenes via a quinomethane generated in situ from a Mannich base
p-Hydroxybenzylation of arenes can be performed efficiently using a Mannich base and (MeO)2SO2 at reflux in the presence of ZnCl2.
Baik, Woonphil,Lee, Hyun Joo,Yoo, Chang Hyun,Jung, Ji Won,Kim, Byeong Hyo
p. 587 - 589
(2007/10/03)

3,9-carbohydrate substituted 2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane phosphite stabilizers
Carbohydrate substituted phosphites of Formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.
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(2008/06/13)

ETUDE DE REACTIONS PAR TRANSFERT MONOELECTRONIQUE ENTRE DIVERS HYDROGERMANES A CARACTERE ACIDE ET DES SYSTEMES QUINONIQUES DIA- ET PARA-MAGNETIQUES
The chlorogermanes PhnCl3-nGe-H (n = 0, 1, 2) were treated with diamagnetic (3,5-di-t-butylorthoquinone) 1 and the paramagnetic galvinoxyl 2.These reactions occur mainly by monoelectron transfer giving the corresponding adducts.In the case of 3,5-di-t-butylorthoquinone, the resulting 1-4 adducts decompose by two simultaneous processes (HCl elimination and redistribution) yielding germadioxolanes.The chlorogermadioxolanes prepared in this way easily cause halogenic redistribution leading to chlorogermanes and germylcatecholates having branched or spiranestructure.In the case of the galvinoxyl radical, the same chlorogermanes lead by monoelectron transfer to the corresponding quinophenol and an intermediate germanium-centered radical.The latter by recombination outside the solvent cage, gives digermane.However, its primary reaction, which occurs within the solvent cage, is with quinophenol to form two isomeric O- and C-germylated catechols.The C-isomer is by far predominant as it also formed in the secondary hydrogermylation of quinophenol produced in the initial stage of the reaction.We have been able to confirm these mechanisms by a comparative study of the reaction of germanium hydrides R3Ge?+-H?-, acidic germanes X3Ge?--H?+, and germanates X3Ge(-)N-H(+) with galvinoxyl and the corresponding quinophenol.Key words: SET reactions; germylations; quinones; chlorohydrogermanes; chlorogermanes; chlorogermanates.
Riviere, P.,Castel, A.,Abdennadher, C.
p. 181 - 194
(2007/10/02)

Etude du transfert monoelectronique entre des germylanions et des piegeurs de spin dia et paramagnetiques
Reactions between organogermyllithium R3GeLi and several substrates favoring SET reactions (3,5-di-t-butyl-orthoquinone, fluorenone, tetracyanoquinodimethane, 2,4,6-tri-t-butylnitrosobenzene, etc.) lead mainly to the formation of digermanes and O- or N-germyl adducts.All these reactions seem to proceed principally by single-electron transfer.An ESR study of the reaction shows transient organic radical anion formation and germanium-centred radicals R3Ge.The prepondancy of this mechanism can be demonstrated by the reaction between R3GeLi and a paramagnetic quinonic species, the galvinoxyl radical: the latter is almost completely transformed into a diamagnetic anion.Digermanes mainly produced in these reactions are formed via radicalar duplication as well as lithiogermolysis of reaction adducts.
Riviere, P.,Castel, A.,Desor, D.,Abdennadher, C.
p. 51 - 60
(2007/10/02)

Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives
1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidine derivatives of s-triazines having functional groups such as hydroxy, amino, carboxy, epoxy, isocyanate or the like present are capable of chemically bonding with polymer substrates having anhydride, epoxide, alkoxymethylmelamine or isocyanate moieties present. This chemical bonding prevents migration or loss of the stabilizer during subsequent processing or end-use application of the stabilized polymer.
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(2008/06/13)

Reinvestigation on the Reaction of 2,6-Di-tert-butylbenzoquinone Methide and 2,6-Di-tert-butylphenol
The reaction of quinone methide 1 and phenol 2 in equimolar amounts was investigated in pentane at 30 deg C.Products were isolated by means of column chromatography on SiO2.There was a marked difference in product distribution between the reactions in the presence and absence of added Et3N.Dienones 3 and 10 were obtained only from the former reaction, while formation of 1,2-bis(4-hydroxyphenyl)ethane 18 and 4,4'-dihydroxybiphenyl 20 was overwhelming in the latter reaction.Other products from both reactions were relatively small quantities of 4,4'-stilbenequinone 17, 4,4'-diphenoquinone 21, and bis(4-hydroxyphenyl)methane 24, but dienone 4 was not obtained.Compounds 20 and 24 obtained from the latter reaction were formed by isomerization of dienones 19 and 23, respectively, during chromatography.The reaction is initiated by dimerization of 1 to generate biradical 11.Subsequent processes involving hydrogenation-dehydrogenation, coupling-dissociation, and dienone-phenol rearrangement account for the formation or the lack of formation of the products.The difference in product distribution is ascribed to capability of Et3N to catalyze the isomerization.Quinone methide 1 also adds to 2 to give 23.The decay of 1 in the presence of both 2 and phenol 6 gave dienone 8 additionally.The formation of 24 and 4 was facilitated by conducting the reaction of 1 and 2 in DMSO.Dehydrogenation of 10 and 3 with PbO2 afforded spirodienones 27 and 28, respectively.Compounds 27 and 28 were unstable, and their decay in solution was investigated in the presence or absence of added 2.The results show that the decay is initiated by homolytic scission of the C-C bond connecting the dienone rings in the cyclopentane (in 27) and cyclohexane (in 28) rings.Compound 28 is novel in that it bears two kinds of such C-C bonds.Reversibility of the dimerization of 1 is suggested.
Omura, Kanji
p. 306 - 312
(2007/10/02)

Mercaptotriazine derivatives as lubricant additives
Compounds of the formula STR1 and of the formula STR2 in which X and X' are, for example, --S--CHR1, --NR2 R3, --S--R3, --NR2 R3 or --OR3, R1 is, for example, --H, alkyl, cycloalkyl or phenyl, R2 and R3 are, for example, --H, alkyl, cycloalkyl or phenyl, or R2 and R3 together form a 3- to 7-membered heterocyclic ring, and R is alkylene, and compositions containing at least one compound of the formulae I and/or II and at least one lubricant, one hydraulic fluid or one metal working fluid, the compounds of the formula I and/or II being used as extreme pressure and wear-reducing additives.
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(2008/06/13)

SUBSTITUTED DIALKYLAMINOMETHYLPHENOLS IN AN EXCHANGE REACTION WITH CARBOXYLIC ACID ANHYDRIDES
Carboxylic acid benzyl esters are formed in the reaction of carboxylic acid anhydrides with N,N-dialkyl-4(2)-hydroxy-substituted benzylamines. 4-Hydroxy-3,5-di-tert-butylbenzyl acetate exchanges an acetyl fragment for an alkoxyl fragment and benzylates phenol derivatives in the presence of an acid.
Nikiforov, G. A.,Bannikov, G. F.,Mal'donado, I. K. A. Romero,Malysheva, R. D.,Ershov, V. V.
p. 2530 - 2535
(2007/10/02)

Sulfur-containing compounds as antioxidants for lubricants and elastomers
Compounds of the formula (I) STR1 in which the Rs independently of one another are H, phenyl, naphthyl or C7 -C30 alkaryl and R1 is H, C1 -C8 alkyl, C7 -C9 aralkyl, C5 -C12 cycloalkyl, phenyl, naphthyl, C7 -C30 alkaryl or a group of the formula (II) R2 is C7 -C30 alkaryl, phenyl, naphthyl or phenyl containing, in the para-position, an HO or C1 -C18 alkoxy group or a group of the formulae STR2 or R1 and R2, together with the nitrogen atom to which they are attached, are a radical of the formula (III) STR3 R3 is a radical of the formulae --(CH2)b --COOR6 or --(CH2)2 OCOR7, a is the number 1, 2 or 3 and b is the number 1 or 2, and R4 is phenyl or a group of the formula (II), the two R5 s independently of one another are H, C1 -C24 alkyl, C5 -C12 cycloalkyl or C7 -C9 aralkyl, and R6 is H, C1 -C18 alkyl or benzyl, R7 is C1 -C14 alkyl, phenyl or a group of the formula in which Y is --O-- or --S--, a is the number 1, 2 or 3 and m is the number 1 or 2, B is a direct bond, --S--, --S--S-- or a C1 -C12 alkylene radical, X in the formula (III) is a direct bond, --S-- or a group of the formulae STR4 form a phenothiazine, phenazine, acridine or carbazole radical.
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(2008/06/13)

1,4-Oxathianones and 1,4-oxathiepanones
The compounds of the formula STR1 in which R is C1 -C24 alkyl, C3 -C20 alkenyl, C5 -C6 cycloalkyl, unsubstituted or C1 -C4 alkyl-substituted phenyl or phenyl-C1 -C4 alkyl, n is 1 or 2, and X is S or O, are highly suitable as additives, in particular as antiwear and high-pressure additives, and as corrosion inhibitors in functional fluids, for example in lubricants, fuels, hydraulic fluids, metal-working fluids and drilling fluids.
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(2008/06/13)

Reaction product of a rosin acid and an antidegradant
There is disclosed a reaction product of a rosin acid and a polyfunctional compound having at least one functional group capable of reacting with a carboxylic acid functionality and another functional group having antidegradant properties. The reaction products of this invention can be used as antidegradants in polymeric compositions and lubricating oil compositions.
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(2008/06/13)

Synthesis and Properties of sym-Triazine Derivatives. 8. Synthesis of Amino and Alkoxy Derivatives of sym-Triazine Containing Fragments of a Sterically-Hindered Phenol from 2,4-Bis(trichloromethyl)-sym-triazines
The reactions of 2,4-bis(trichloromethyl)-6-substituted sym-triazines with several amino and hydroxy derivatives of 2,6-di-tert-butylphenol were studied.It is shown that, depending on the reaction conditions, one or both trichloromethyl groupings in the starting sym-triazines are replaced.
Kelarev, V. I.,Yakh'ya, F. Laauad,Karakhanov, R. A.,Golubeva, I. A.,Vishnyakova, T. P.,Malova, O. V.
p. 556 - 561
(2007/10/02)

ESR SPECTRA AND KINETICS OF THE DISPROPORTIONATION OF SUBSTITUTED PHENOXY RADICALS. COOMUNICATION 2. RADICALS OF 2,4,6-TRIALKYLSUBSTITUTED MONO-, p-BIS-, p-TRIS-, AND p-TETRAPHENOLS
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Roginskii, V. A.
p. 1833 - 1841
(2007/10/02)

REACTION OF 2,6-DI-TERT-BUTYLPHENOL WITH METHYL ACRYLATE IN THE PRESENCEOF BASES
The alkylation of methyl 2-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate with methyl acrylate in the presence of lithium hydride at 160 deg C leads to derivatives of glutaric and trimethoxycarbonylhexanoic acids.The latter were detected in the products from the reaction of 2,6-di-tert-butylphenol with methyl acrylate or methyl β-methoxypropionate in the presence of bases.The composition of the reaction products was studied in relation to the nature of the solvent.
Titova, T. F.,Krysin, A. P.,Bulgakov, V. A.,Mamatyuk, V. I.
p. 1732 - 1737
(2007/10/02)

Reactions of 4-Hidroxycyclohexa-2,5-dienones under Acidic Conditions
The 4-hydroxy-4-phenyl-2,6-di-t-butylcyclohexa-2,5-dienone (2) undergoes reaction in acidic conditions to give, inter alia, derivatives of an arene-1,2-diol.In poorly nucleophilic media, the 1,1'-biphenyl-4-ol (16) and the 5-phenyl-o-benzoquinone (37) are the main products.Isolation of the 4-(2-methylpropyl)cyclohexadienone derivatives (41) and (42) provides the first examples of intermolecular trapping of a four-carbon unit.The products are consistent with the intervention of the phenoxenium ion (44); the formation of the 2-methyl-1,3-benzodioxole (43) testifies to the intermediacy of such a powerful oxidant.Whereas the 4- phenyl-2-t-butyl-p-quinol (5) gave a complex mixture from which only the 1,1'-biphenyl-4-ol derivative (24) was isolated, the 2,6-di-isopropyl- and 2,6-dimethyl-analogues (4) and (6) afforded mainly the arene-1,3-diol derivatives (48) and (47), respectively.The 4-methyl-2,6-di-t-butyl-p-quinol (7) gave products arising from nucleophilic attack on an intermediate p-quinone methide; dimers were the major products in the absence of a good nucleophile.
Davis, Brian R.,Gash, Diana M.,Woodgate, Paul D.,Woodgate, Sheila D.
p. 1499 - 1508
(2007/10/02)