Benzenediols Resorcinol

Very recently, MacGillivray et al. succeeded in the supramolecular construction of molecular ladders in the solid state using a linear template approach [48]. They designed the cocrystals 1,3-benzenediol (resorcinol) or a derivative with an all-trans-bis(4-pyridyl)butadiene or hexatriene, in which two resorcinol molecules preorganize two polyene molecules through two hydrogen bond interactions, for [2-1-2] photoaddition (Scheme 5). In this design, two polyenes would... 

Exercise 26-3 Treatment of 1,3-benzenediol (resorcinol) with an ammonia-ammonium chloride solution under pressure at 200° (no sulfite) gives 3-amino-benzenol. Write a reasonable mechanism for this transformation. Would you expect benzenol itself to react similarly Why ... 

Exercise 26-7 1,3-Benzenediol (resorcinol) can be converted to a carboxylic acid with carbon dioxide and alkali. Would you expect 1,3-benzenediol to react more, or less, readily than benzenol Why Which is the most likely point of monosubstitution Explain. 

Phenols may have more than one hydroxy group attached to the same benzene ring - for example, the three isomeric dihydroxybenzenes catechol (ortho-dihydroxy-benzene or 1,2-benzenediol), resorcinol (meta-dihydroxy-benzene or 1,3-benzenediol) and hydroquinone (para-dihydroxybenzene or 1,4-benzenediol) see Figure 25.3. 

Although there are ten isomeric naphthalenediols, there are enthalpy of formation data for only five of them. The enthalpy of formation data for the 1,4-isomer from two sources are disparate, as are the data from the two sources for the 2,3-isomer. The 1,3-naphthalenediol is more stable than either the 1,2- or the 1,4-diols for the same reason that the m-benzenediol, resorcinol, is more stable than its isomers more stable resonance structures for 1,3-dihydroxy substitution on an aromatic ring. From the appropriate OH/H increment exchange energies and the enthalpy of formation of naphthalene, we would have predicted a value of —329 kJ moE and —208 kJ mol for any solid and gaseous naphthalenediol, respectively. Only for 1,3- and 2,7-naphthalenediol is the expectation confirmed the others with their less stable ortho- and para-type substitution are less negative. 

H.24) 1,3-Benzenediol, resorcinol, resorcin, 1,3-dihydroxybenzene, m-hydroquinone 1108-46-3] FEMA 3589... 

It is obvious that more than one functional group may be attached to a benzene ring. In some cases, the presence of two or more functional groups leads to a special name for that compound. One such case occurs when an benzene ring contains two hydroxyl groups. Each of these compounds has an lUPAC name based on the rules just discussed, but many have a unique common name. The ortho compound (34) is named 1,2-benzenediol, but its common name is catechol. The meta compound is named 1,3-benzenediol (resorcinol) and the para compound is named 1,4-benzenediol (hydroquinone). 

Polyhydric phenols with more than two hydroxy groups (ie, the three positional isomers of benzenetriol, the three isomeric benzenetetrols, benzenepentol [4270-96-6] and benzenehexol [608-80-0]) are discussed in this article. The benzenediols are catechol, resorcinol, and hydroquinone (see Hydroquinone, RESORCINOL, AND CATECHOL). 

The close electrochemical relationship of the simple quinones, (2) and (3), with hydroquinone (1,4-benzenediol) (4) and catechol (1,2-benzenediol) (5), respectively, has proven useful in ways extending beyond their offering an attractive synthetic route. Photographic developers and dye syntheses often involve (4) or its derivatives (10). Biochemists have found much interest in the interaction of mercaptans and amino acids with various compounds related to (3). The reversible redox couple formed in many such examples and the frequendy observed quinonoid chemistry make it difficult to avoid a discussion of the aromatic reduction products of quinones (see Hydroquinone, resorcinol, and catechol). 

Benzenedisulfonic acid [831-59-4] (disodium salt), produced by the neutralization of the disulfonic acid with sodium sulfite [7757-83-7] is used in the manufacture of resorcinol [108-46-3] (1,3-benzenediol) (2), a chemical component found in mbber products and wood adhesives (72). The disodium salt is fused with sodium hydroxide, dissolved in water, and acidified to produce resorcinol, which is isolated via extraction (73). 

Kluge C, A Tschech, G Fuchs (1990) Anaerobic metabolism of resorcylic acids (m-dihydroxybenzoates) and resorcinol (1,3-benzenediol) in a fermenting and in a denitrifying bacterium. Arch Microbiol 155 68-74. 

Flickinger CW. 1976. The benzenediols Catechol, resorcinol and hydroquinone - A review of the industrial toxicology and current industrial exposure limits. Am Ind Hyg Assoc J 37 596-606. 

Flickenger CW The benzenediols Catechol, resorcinol and hydroquinone—Review of the... 

Chem. Abstr. Serv. Reg.No.. 108-46-3 Chem. Abstr. Name. 1,3-Benzenediol lUPAC Systematic Name. Resorcinol Synonyms. meto-Benzenediol resorcin... 

Raney cobalt alloy, see Aluminium—cobalt alloy, 0049 Raney nickel alloys, see Aluminium—nickel alloys, 0055 Resorcinol diacetate, see 1,3-Diacetoxybenzene, 3285 Resorcinol, see 1,3-Benzenediol, 2325 Rhenium hexafluoride, 4367 Rhenium hexamethoxide, 2599 Rhenium nitride tetrafluoride, 4338 Rhenium, 4884... 

In the photometric determination of copper, a coupling product formed between the diazonium salt from 2-amino-pyridine and resorcinol, or 4-(2-pyridinylazo)-l,3-benzenediol 21, has been used. Here the formed copper complex under acetate buffer exhibits an absorption peak at 520 nm, which is measured photometrically <2003KPU28>. Similarly for photometric determination of iron(ll), a coupling product formed between the diazonium salt of 2-amino-4,6-dihydroxypyrimidine and 8-hydroxyquinoline, or 6-hydroxy-2-(8-hydroxy-7-quinolinyl)azo-4(l//)-pyrimidinone 22, has been used. This reagent forms a blue complex with iron(n) ions with an absorption maximum at 625 nm that does not interfere with the presence of other metals <2003KD95>. 

SYNS 1,3-BENZENEDIOL, 2,4,6-TRINITRO-, BARIUM SALT, HYDRATE (2 1 1) RESORCINOL, 2,4,6-TRINITRO-, BARIUM SALT, HYDRATE (2 1 1)... 

The three monohydroxy derivatives of phenol are all well-known componnds, the o-, m- and p-species with the long-established, trivial names catechol, resorcinol and hydro-quinone. These compounds are all benzenediols and, as snch, they and their snbstimted derivatives will be discussed later in this text. 

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