Synthesis of 2-Hydroxybenzo[a]pyrene, a Tumorigenic Phenol Derivative of Benzo[a]pyrene

Autor:	Bukowska Maria, Harvey RonaldG.
Rok vydání:	1992
Předmět:	Polymers and Plastics Organic Chemistry Succinic anhydride Clemmensen reduction chemistry.chemical_compound Dimethyl sulfate Benzo(a)pyrene chemistry Materials Chemistry Organic chemistry Pyrene Dehydrogenation Derivative (chemistry) Demethylation
Zdroj:	Polycyclic Aromatic Compounds. 2:223-228
ISSN:	1563-5333 1040-6638
DOI:	10.1080/10406639208048423
Popis:	An efficient synthesis of 2-hydroxybenzo[a]pyrene (1a) from 4,5,9,10-tetrahydropyrene via 2-methoxy-4,5,9,10-tetrahydropyrene (2e) is described. Friedel–Crafts acetylation of tetrahydropyrene affords the 2-acetyl derivative which is transformed to the 2-methoxy derivative 2e via Baeyer–Villager oxidation, hydrolysis, and treatment with dimethyl sulfate. Friedel–Crafts succinoylation of 2e with succinic anhydride and AlCl3 takes place regiospecifically in the 7-position. The product is transformed to 1a via Clemmensen reduction, HF cyclization, Wolff–Kishner reduction, catalytic dehydrogenation, and demethylation with HBr.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::eff692600d84714473966c5163a42b44 https://doi.org/10.1080/10406639208048423 Zobrazit plný text záznamu