Abstract
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-tolyI-4-cyclopentenone (13), the hydrogenation of which over palladium charcoal gave 14.
