My best try was to use aldol condensation after the reduction of the substrate(cyclopentanol) but that gives me a product with a methylphenyl substituent(2-Phenylcyclopentanone), nor a phenyl only.
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1$\begingroup$ This can be done in quite a few ways. It would be helpful if you told us what level of organic chemistry you were in to provide context for what types of reactions you have likely learned about. $\endgroup$– ZheMay 22, 2017 at 3:17
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1$\begingroup$ @zhe now I'm studying reactions in alcohols, I already know about Sn1,Sn2,E1 and E2 reactions as like any reactions involving reductions and oxidation of functional groups. Actually, I'm learning nucleofilic substitutions. If you give one or more ways of proceeding that I don't fully understand, I will study that. $\endgroup$– Mattheus Sant'AnnaMay 22, 2017 at 3:28
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2 Answers
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Step 1 dehydrate cyclopentanol to cyclopentene with conc Sulfuric acid
Step 2 epoxidise cyclopentene with m- Chloroperbenzoic acid
Step 3 open the epoxide with phenyl grignard to give 2-phenyl cyclopentanol
Step 4 oxidise to required product
answered May 22, 2017 at 17:00
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1) oxidise using your favourite method (pyridinium dichromate; metal catalyst and oxygen; hypochlorous acid etc.) to cyclopentanone. 2) Pd catalysis using a bidentate ligand e.g. DPPF, with a hindered base, coupling the cyclopentanone to PhBr, to give the alpha-arylated product. See JACS 1997, 119, p.12382 by John Hartwig. This method works with isopropyl ketones also
