title: An efficient and expeditious synthesis of novel 2,2-dialkyl-2,3-dihydrobenzofurans from phenols and 2,2-dialkylacetaldehydes.
abstract: Reactions of 2,2-dialkylaldehydes with electronrich 2-naphthols and para-substituted phenols in presence of catalytic amount of p-TSA under closed vessel solvent-free microwave irradiation conditions resulted in formation of corresponding 2,2-dialkyl-1,2-dihydronaphtho[2,1-b]furans and 2,2-dialkyl-2,3-dihydrobenzofurans, respectively, in good to excellent yields. The effect of stoichiometry, temperature, and catalyst in reaction progress was systematically investigated. 14-Alkyl-14H-dibenzo[a, j]xanthenes was obtained as minor productswhen 2-naphthol and 6-bromo-2-naphthols were used as starting phenols. Simple phenols gave a lower yield of the 2,2-dialkyl-2,3-dihydrobenzofurans products than their electron-rich naphthalene counterparts. Also, xanthene-type products were not detected in case of simple phenols by GC–MS or column chromatography.
authors.affiliation: Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada. ajha@acadiau.ca
authors.forename: Amitabh
authors.initials: A
authors.lastname: Jha
authors.forename: Ting-Yi
authors.initials: TY
authors.lastname: Chou
authors.forename: Doug
authors.initials: D
authors.lastname: Vaughan
mesh_terms: D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis*; D002384:Catalysis; D008401:Gas Chromatography-Mass Spectrometry; D008872:Microwaves; D009284:Naphthols / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature; D014966:Xanthenes / Q000138:chemical synthesis
chemical_list: D001572:Benzofurans; D009284:Naphthols; D010636:Phenols; D014966:Xanthenes; D000079:Acetaldehyde