Abstract
2-Ketocyclohexylacetic acid and 2-ketocyclohexyl-α-propiomc acid were prepared by the condensation of the sodio-derivative of ethyl cyclohexanone-2-carboxylate with ethyl bromoacetate and ethyl α-bromopropionate, respectively, followed by hydrolysis. This method of condensation is not successful with ethyl α-bromo-β-phenylpropionate. It also fails with α-bromo-esters of dibasic acids such as ethyl bromomalonate and ethyl bromosuccinate.The γ-lactones of cyclohexanolacetic acid and cyclohexanol-α-propionic acid result from Reformatsky reactions between cyclohexanone and ethyl bromoacetate and ethyl α-bromopropionate, respectively, followed by treatment with mineral acid. Ethyl bromomalonate and ethyl bromosuccinate fail to react with cyclohexanone in either Reformatsky or Grignard reactions.
Published Version
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