75787-28-9Relevant academic research and scientific papers
Lewis Acid Catalysed Reactions of Coumarins: 7-Methoxy-8-(3'-methylbut-2'-enyl)coumarin (Osthol) and 7-Methoxy-8-(1',2'-epoxy-3'-methylbut-3'-enyl)coumarin (Phebalosin) and PMR Identification of Friedel-Crafts Reaction Products of Toluene and Xylene
Banerji, J.,Bhaduri, N.,Rej, R. N.,Shoolery, J. N.,Mukherjee, S.,Bhattacharya, S.
, p. 341 - 345 (2007/10/02)
The transformation of the coumarins, 7-methoxy-8-(3'-methylbut-2'-enyl)coumarin (Osthol, I) and 7-methoxy-8-(1',2'-epoxy-3'-methylbut-3'-enyl)coumarin (phebalosin, XV) in the presence of various Lewis acids has been studied.Osthol (I) on treatment with anisole in the presence of aluminium chloride affords 7-methoxy-8-(3'-anisyl)isopentyl-(V)- and 7-methoxy-8-(3'-p-hydroxyphenyl)isopentyl-(VI)-coumarins in addition to 7-hydroxy-8-isopentylcoumarin (IV) while with chlorobenzene as solvent the usual disproportionation product (IV) is produced.It is further observed that toluene is converted into 2,7-(VIII)- and 2,6-(IX)-dimethyl anthracenes and xylene (o-,m- and p-) into 2,3,6,7-tetramethylanthracene (X), all these compounds being characterised from their detailed NMR analysis.Phebalosin (XV) in the presence of boron trifluoride etherate furnishes 7-methoxy-8-(1'-formyl-2'-methylprop-1'-enyl)coumarin (XVI) while with boron tribromide 2'-bromoseselin is produced.
