76650-22-1Relevant academic research and scientific papers
Thermal Rearrangement of 2-Methyl-2-(2'-acetoxy-5'-methylphenyl)oxirane
Dhekne, Vijay V.,Rao, A. S.
, p. 852 - 855 (2007/10/02)
Thermal rearrangement of 2-methyl-(2'-acetoxy-5'-methylphenyl)oxirane (2) at 160 deg C for 1 hr furnishes a mixture of 2-(2'-hydroxy-5'-methylphenyl)propenyl acetate (4), 3,5-dimethylbenzofuran (11), 2-(2'-acetoxy-5'-methylphenyl)-propenyl acetate (5), 2-hydroxy-5-methylacetophenone (13), (+/-)-2,3-dihydro-3α,5-dimethylbenzofuran-2β-ol (14) and (+/-)-2,3-dihydro-3β,5-dimethylbenzofuran-2β-ol (15).Evidences in support of E-geometry at the ethylenic linkage of enolester (4) are presented.Treatment of 4 with alkali in the presence of air furnishes 13.Oxidation of a mixture of 14 and 15 gives 2,3-dihydro-3,5-dimethylbenzofuran-2-one (19). 3,5-Dimethylbenzofuran (11) has been prepared from 4.Thermal rearrangement of 2-methyl-(2'-acetoxy-5'-bromophenyl)oxirane (27) furnishes 5-bromo-3-methylbenzofuran (12) in good yield.
