Resorcinol 1.3- dihydroxybenzene

Resorcinol (1,3-dihydroxybenzene) is more reactive to formaldehyde than phenol itself, the two hydroxyl groups reinforcing each other in activating the o-and p-positions. This allows faster reactions to occur than with phenol, when compared at the same temperature, and under appropriate conditions curing can occur at normal room temperatures. 

Phillip B, B Schink (1998) Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1,3-dihydroxybenzene) by the denitrifying bacteiimn Azoarcus anaerobius. J Bacteriol. 180 3644-3649. 

During the very first series of studies using single-crystal x-ray crystallography to determine the structures of organic molecules, Robertson reported the structure of resorcinol (1,3-dihydroxybenzene) [25]. This crystalline material corresponded to that ordinarily obtained at room temperature, and was later termed the a-form. Shortly thereafter, it was found that the a-form underwent a transformation into a denser crystalline modification (denoted as the P-form) when heated at about 74°C,... 

With this purpose, several different types of solid acid catalysts have been investigated for the acylation of aromatics, but the best performances have been obtained with medium-pore and large-pore zeolites (3-9). In general, however, the use of acylating agents other then halides, e.g., anhydrides or acids, is limited to the transformation of aromatic substrates highly activated towards electrophilic substitution. In a previous work (10), we investigated the benzoylation of resorcinol (1,3-dihydroxybenzene), catalyzed by acid clays. It was found that the reaction mechanism consists of the direct 0-benzoylation with formation of resorcinol monobenzoate, while no primary formation of the product of C-benzoylation (2,4-dihydroxybenzophenone) occurred. The latter product formed exclusively by... 

Problem 15.58 Translate the following description into a chemical equation Friedel-Crafts acylation of resorcinol( 1,3-dihydroxybenzene) with CH,(CH2)4COCI produces a compound which on Clemmensen reduction yields the important antiseptic, hexylresorcinol. 

Resorcinol (1,3-Dihydroxybenzene) (BUA Report 99), Stuttgart, S. Hirzel Wissenschaftliche... 

Examples include resorcinol (1,3-dihydroxybenzene 1.2), a meta-dihydroxylated simple phenolic, and phloroglucinol (1,3,5-trihydroxybenzene 1.3), a meta-trihydroxylated simple phenolic. 

Recent work by Len MacGillivray of the University of Iowa, USA, has used topochemistry to produce an impressive range of new solid compounds by the addition of hydrogen bonded templates in order to bring about the designer orientations of photochemically reactive molecules in the solid state.34 A simple example is the use of resorcinol (1,3-dihydroxybenzene) to position two molecules of trans 1,2 bis (4-pyridyl) ethylene with their double bonds overlapping at ca. 4 A as required by the topochemical postulate. Upon photolysis the product rcfHetrakis(4-pyridyl)cyclobutane is formed stereospecifically and in 100 % yield, Scheme 8.2. In the absence of the resorcinol template trans-l,2-bis(4-pyridyl) ethylene is... 

Antiseptic plant-derived phenols include phenol (Phe-OH, hydroxybenzene, carbolic acid), />-cresol (4-methylphenol), catechol (1,2-dihydroxybenzene), resorcinol (1,3-dihydroxybenzene) and pyrogallol (1,2,3-trihydroxybenzene). Other simple phenols with antimicrobial properties include some related to benzoic acid (benzenecarboxylic acid), namely salicylic acid (2-hydroxybenzoic acid), ginkgoic acid (2-hydroxy-6-(pentadec-8-enyl)benzoic acid), gentisic acid (2,5-dihydroxybenzoic acid), pyrocatechuic acid (3,4-dihydroxybenzoic acid) and gallic acid (3,4,5-trihydroxybenzoic acid). Other plant-derived phenol-related compounds include 4-methylcatechol, 1,3-dihydroxy-5-(heptadec-12-enyl)benzene, hydroquinone (1,4-dihy-droxybenzene), 1,4-dihydroxy-2-geranyl (di-isoprenyl)benzene and 4-methoxybenzaldehyde (/>-anisealdehyde). 

Reported vapor pressures of resorcinol (1,3-dihydroxybenzene) at various temperatures and the coefficients for the vapor pressure equations... 

Resorcinol (1,3 -Dihydroxybenzene) Hydroquinone (1,4-Dihydroxybenzene) 2-Methoxyphenol (Guaiacol)... 

The discoveries of the isomeric dihydric phenols were as old as that of phenol itself. Catechol,(1,2-benzenediol, 1,2-dihydroxybenzene, o-dihydroxybenzene) was first obtained in 1839 essentially from the dry distillation of tannin. Resorcinol (1,3-dihydroxybenzene), was isolated in 1864 from the alkaline fusion of galbanum, and of asafoetida, resins, repectively from Iranian species of Ferula and Narthex asafoetida. In 1820 hydroquinone was recovered from the dry distillation of quinic acid although it was not investigated structurally until 1844 by Wohler. 

Predict the structure of the major product from the interaction of resorcinol (1,3-dihydroxybenzene) and (i) PhCOCH2COMe in AcOH/HCl (ii) methyl 2-oxocyclopentanecarboxylate/H2S04. 

Resorcinol (1,3-dihydroxybenzene [CAS 108-46-3]) Corrosive acid and protein denaturant extremely Irritating upon direct contact severe burns result. May cause methemoglobinemia (see p 261). A sensitizer. Dermally well absorbed, See also phenol, p 302. 10 ppm - 1 0 White crystalline solid with a faint odor, May turn pink on contact with air. Vapor pressure Is 1 mm Hg at 108°C (226°F). Combustible,... 

Porous carbon gels prepared by polycondensation of hydroxylated benzene (phenol, catechol, resorcinol, hydroquinone or phloroglucinol,. ..) and aldehyde (formaldehyde, furfural,...) in a solvent followed by drying and pyrolysis have been extensively studied for the past fifteen years [51-66, 101], Various carbon materials whose texture depends on the nature of the precursors, the gelation conditions and the drying method can be obtained. The most common precursors are resorcinol (1,3-dihydroxybenzene) and formaldehyde (CHjO) and the polymer is usually synthesized using water as solvent and sodium carbonate (NUjCOj) as catalyst. 

Calixarenes, for example, 2.120, have already been discussed as hosts for cations and both cation and neutral molecules simultaneously in Sections 2.3.6 and 2.5.5, respectively. Resorcarenes e.g. 2.121) are very closely related to calixarenes and are sometimes referred to as calixresorcarenes. They are prepared from the acid-catalysed condensation of resorcinol (1,3-dihydroxybenzene) with aldehydes, a reaction first carried out by Baeyer in 1872. This macrocycle is arguably one of the most important molecules in the field, as resorcarenes serve as the basic building blocks for many cavitands and (hemi)carcerands. Both calixarenes and resorcarenes posses a shallow bowl-shaped conformation in their most stable forms. However, [4]resorcarenes (the [4] prefix refers to the ntimber of resorcinol units that make up the molecule, just as in calix[n]arenes) tend to produce a... 

Keto-enol tautomerism has been studied by computation for a range of polyphenols such as resorcinol (1,3-dihydroxybenzene) and phloroglucinol (1,3,5-trihydroxy-benzene). In addition to the obvious favouring of enols associated with aromaticity, less obvious through-bond effects are also highlighted. 

Resorcinol (1,3-dihydroxybenzene) 159 and chlorosulfonic acid (five parts) in carbon disulfide at 0 °C or room temperature gave the 4,6-disulfonic acid 160 while with a larger excess of the reagent (ten parts) at room temperature, the 4,6-disulfonyl chloride 161 was isolated (Equation 52). When resorcinol 159 was heated with a very large excess of chlorosulfonic acid (50 parts) at 110 °C for 2 hours, the product was the 2,4,6-trisulfonyl chloride 162 and when the mixture was subjected to even more drastic reaction conditions (160-170 °C, 110 hours), the product was hexachlorobenzene. The rapid addition of chlorosulfonic acid (two equivalents) to resorcinol 159 in nitrobenzene at 15-75 °C precipitates pure 2,4-dihydroxybenzenesulfonic acid in almost quantitative yield. 

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