77196-48-6Relevant articles and documents
Synthesis of 2-Hydroxy-3-p-tolyl-2-cyclopentenone and Its Application to Isolaurene
Tomari, Kennosuke,Machiya, Kozo,Ichimoto, Itsuo,Ueda, Hiroo
, p. 2135 - 2138 (2007/10/02)
2-Hydroxy-3-p-tolyl-2-cyclopentenone (7), a potential starting material for synthesis of isolaurene (1), was prepared by photolysis of 2-p-toluenesulfonyloxy-2-cyclopentenone (6).Conversion of 7 into 2,5-dimethyl-2-p-tolyl-cyclopentanone (14) was carried out as follows.Methylation of 7 with methyl iodide gave 2-methoxy-3-p-tolyl-2-cyclopentanone (9), and the treatment of (9) with methyl magnesium iodide afforded 2-methyl-5-p-tolyl-2-cyclopentenone (11).This compound was allowed to react with methyl iodide in the presence of sodium methoxide to yield 2,5-dimethyl-2-p-tolyl-4-cyclopentenone (13), the hydrogenation of which over palladium charcoal gave 14.