356. Some derivatives of hydroxyquinol, including a synthesis of pyrylium salts of anthocyanidin type. Part XXII

Healey, M.; Robinson, R. A.

doi:10.1039/jr9340001625

Cited by 15 publications

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“…Materials. Hydroxyquinol (1,2,4-trihydroxybenzene) was obtained by hydrolysis of its triacetate (18) and was purified by filtering its ethereal solution through decolorizing carbon and crystallizing the product from ether-petroleum to give off-white crystals (melting point, 141 C; decomposition). Clemmenson reduction of 2,4-dihydroxybenzaldehyde gave 4-methylresorcinol (2).…”

Section: Methodsmentioning

confidence: 99%

Metabolism of resorcinylic compounds by bacteria: orcinol pathway in Pseudomonas putida

Chapman¹,

Ribbons²

1976

J Bacteriol

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Enrichment cultures yielded two strains of Pseudomonas putida capable of growth with orcinol (3,5-dihydroxytoluene) as the sole source of carbon. Experiments with cell suspensions and cell extracts indicate that orcinol is metabolized by hydroxylation of the benzene ring followed successively by ring cleavage and hydrolyses to give 2 mol of acetate and 1 mol of pyruvate per mol of orcinol as shown: orcinol -+ 2,3,5-trihydroxytoluene --2,4,6-trioxoheptanoate -* acetate + acetylpyruvate --acetate + pyruvate. Evidence for this pathway is based on: (i) 975 on August 11, 2020 by guest

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Section: Methodsmentioning

confidence: 99%

Metabolism of resorcinylic compounds by bacteria: orcinol pathway in Pseudomonas putida

Chapman¹,

Ribbons²

1976

J Bacteriol

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“…In the case of hydroxyquinol (m.p. 1380; prepared according to Vliet, 1925 andHealy &Robinson, 1934) good yields of the ester were obtained only if Na2CO3 were used instead of NaOH.…”

Section: Preparation Of Reference Compoundsmentioning

confidence: 99%

Studies in detoxication. 20. The metabolism of benzene. II. The isolation of phenol, catechol, quinol and hydroxyquinol from the ethereal sulphate fraction of the urine of rabbits receiving benzene orally

Porteous

Williams

1949

Biochemical Journal

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TheHoesch Synthesis*Present address, Fuld Bros, Inc.

Spoerri¹

2011

Organic Reactions

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The Hoesch synthesis consists in the condensation of a nitrile with a phenol, a polyhydric phenol, or a phenolic ether to form a hydroxyaryl or alkoxyaryl ketone. Usually, equimolar quantities of the reactants are dissolved in dry ether, preferably in the presence of a catalyst such as zinc chloride and dry hydrogen chloride is introduced. When phenols are used, imino ether hydrochlorides are sometimes formed as by‐products and represent the only product of the reaction. The Hoesch synthesis has proved to be the most convenient synthetic method for certain polyhydroxyacylphenones and polyhydroxybenzophenones. Among these hydroxy ketones are anthelmintics, antidiarrhetics, and antiseptics. Extensions of the Hoesch synthesis are covered in this chapter.

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356. Some derivatives of hydroxyquinol, including a synthesis of pyrylium salts of anthocyanidin type. Part XXII

Cited by 15 publications

References 0 publications

Metabolism of resorcinylic compounds by bacteria: orcinol pathway in Pseudomonas putida

Metabolism of resorcinylic compounds by bacteria: orcinol pathway in Pseudomonas putida

Studies in detoxication. 20. The metabolism of benzene. II. The isolation of phenol, catechol, quinol and hydroxyquinol from the ethereal sulphate fraction of the urine of rabbits receiving benzene orally

TheHoesch Synthesis*Present address, Fuld Bros, Inc.

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