2-Methyl-3-buten-2-ol → 6-Methyl-5-hepten-2-one

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Apart from the improvements according to the present invention, this process has been disclosed by Teisseire et al. "Recherches," June 1956, page 31. The yield is only about 56%, which is entirely inadequate for industrial syntheses. If, instead of an alkyl acetoacetate, diketene is reacted with 2-methyl-3-buten-2-ol in the presence of aluminum triisopropylate, 2-methyl-2-hepten-6-one is obtained in a yield of 83% (cf. "Advances in Organic Chemistry," Volume II, 1960, page 246). It is to be deduced from the last-mentioned publication that for the manufacture of 2-methyl-2-hepten-6-one, diketene is to be preferred over an alkyl acetoacetate as the starting material. This is undoubtedly true on a laboratory scale, but unacceptable for the industrial manufacture of methylheptenone. For safety reasons alone, the instability of diketene demands the use of expensive apparatus. In addition, in order to achieve high yields and smooth operation of the plant, measures are required which substantially cancel out the advantage of the good yield. Further, German Pat. No. 1,068,696 discloses the preparation of 2-methyl-2-hepten-6-one by passing 2-methyl-3-buten-2-ol into a reaction mixture which has been preheated to 160°-250° C. and comprises an alkyl acetoacetate, a mixture of an alkyl acetoacetate and an inert solvent, or a mixture of 2-methyl-3-buten-2-ol, an alkyl acetoacetate and a solvent. However, this process also gives yields of only from 63 to 66% of theory, based on alkyl acetoacetate converted.

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