ChemistryGhost
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phenylcyclopentylaceticacid synthesis? (and it's esters)
I was wondering if it was possible to synthesize phenylcyclopentylaceticacid. Is it?
Maybe using phenylaceticacid and cyclopentyl bromide as reactants with sodium hydroxide?
Or phenylaceticacid methyl ester and cyclopentyl bromide as reactants for cyclopenylphenylacetic acid methyl ester?
"Imagination is more important than knowledge" ~Einstein
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Crowfjord
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I don't see why not. The ester would be the better starting point, otherwise the main reaction would just be the acid-base reaction on the phenyl
acetic acid. Anhydrous conditions and a stronger base like sodium ethoxide or sodium hydride would be necessary, also.
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kmno4
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Reaction of phenylacetonitrile with cyclopentyl bromide under PTC conditions will give α-subtituted nitrile of your acid.
It can be easily converted to the acid or its ester.
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CuReUS
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take care that you keep the elimination side reaction to the minimum(cyclopentyl bromide to cyclopentene) .If you use sodium ethoxide,some trans
esterification might occur so soda amide or sodium hydride is better,and LiNH2 which is an alternative to soda amide can be made from OTC
chemicals
[Edited on 24-1-2015 by CuReUS]
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