74285-43-1

Upstream product

• 106-38-7 para-bromotoluene 
• 74285-41-9 2-Benzyloxy-3-methyl-2-cyclopentenone 
• 3008-40-0 cyclopentane-1,2-dione 
• 10088-87-6 4,5-dioxo-cyclopentane-1,3-dicarboxylic acid diethyl ester 
• 77196-48-6 4,5-Dioxo-1-p-tolyl-cyclopentane-1,3-dicarboxylic acid diethyl ester 
• 77183-95-0 2-p-toluenesulfonyloxy-2-cyclopentenone 
• 77196-49-7 2-methoxy-3-p-tolyl-2-cyclopentenone 
• 77183-96-1 2-hydroxy-3-p-tolyl-2-cyclopentenone 
• 6293-68-1 bis(4-methylphenyl)iodonium bromide 
• 80-71-7 2-hydroxy-3-methylcyclopent-2-en-1-one 

Relevant academic research and scientific papers

Synthesis of 2-Hydroxy-3-p-tolyl-2-cyclopentenone and Its Application to Isolaurene

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.

Synthesis of Isolaurene and Its Related Compounds from Cyclotene

Novel syntheses of isolaurene (1), an isomer of laurene (2) found in algae, and its related compounds were performed from cyclotene (3).Benzylated cyclotene (4) was allowed to react with p-tolyl-magnesium bromide to give 5-methyl-2-p-tolyl-2-cyclopentenon