Compounds Having a Cycloalkylene Chain

Patent Cyclic Compounds Having a Cycloalkylene Chain 

Langlosis etal, US Patent 6,583,319 (June 24, 2003) Assignee Les Laboratoires Servier Utility Preventing and Treatment of Sleep Disorders 

7-Methoxy-naphtha-l-yl-acetic acid (0.225 mol) was dissolved in a mixture of 700 ml benzene and 300 ml HOAc and Pb(OAc)4 (0.225 mol) added. The mixture heated to 60-70 °C, refluxed 30 minutes, cooled, concentrated, extracted with 200 ml CHjClj. 500 ml Diethyl ether was added causing a creamy white precipitate which was filtered through Celite. The ethereal solution was dried and concentrated from which the product recrystallized when chilled and was isolated. 

The product from Step 1 (0.15 mol) was dissolved in 300 ml methyl alcohol containing KOH (0.60 mol) and the mixture stirred 3 hours at ambient temperature. The mixture was hydrolyzed over ice containing concentrated HCl, the precipitate isolated, dried, re-crystallized in a mixture of CH2CI2 and cyclohexane, and the product isolated as white crystals. 

The product from Step 2 (0.10 mol) was dissolved in 300 ml CH2CI2 and manganese oxide (65 g) added in three stages (t = 0,25g t = 90 minutes, 25 g and t = 24 hours, 15 g). The mixture was filtered over silica gel to yield an oil which solidified upon cooling. 

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