Method for preparing bis allyl alcohol compound 4-(3-methyl phenyl)-1,6-heptadiene-4-alcohol

Abstract

The invention provides a method for synthesizing diallyl alcohol compound as 4-(3-methyl phenyl)-1, 6-heptadiene-4-alcohol, which uses allyl zine bromide and mtoluie chloride or mtoluie ethyl formate as raw materials to be reacted at room temperature, extracts via ether, dries and evoprates out solvent and separates via column chromatography to obtain the product. The invention has short synthesis route, high efficiency, high reaction yield (at least 92%), which can eliminate solvent and catalyst and use cheap and non-toxic metal zinc, thereby effectively avoiding the pollution of organic solvent and catalyst to protect environment. The invention has mild reaction conditions (room temperature), short reaction time, simple operation, reduced energy consumption, reduced synthesis cost and significant benefit for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to a method for preparing diallyl alcohol compounds, in particular to a diallyl alcohol compound 4-(3-methylphenyl)-1,6-heptadiene The preparation method of -4-ol. Background technique [0002] Allyl alcohol is a kind of alcohol with unsaturated substituent allyl group, it is a very active chemical synthesis intermediate, especially the monoallyl alcohol produced by monoallylation and bisallylation (homoallylicalcohol) and diallylic alcohol (diallylic alcohol) play a very important role in the synthesis of various compounds (such as hydrocarbyl lactone and spironolactone). [0003] People have studied the synthesis of monoallyl alcohol for many years, but the research and synthesis of diallyl alcohol has developed to a certain extent in the past ten years. In 1997, Béatrice Hamann-Gaudinet et al. (Tetrahedron Letters, 1997, 38, 6585-6588) reacted ethyl carboxylate with allyl samariu...

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Problems solved by technology

In 1997, Béatrice Hamann-Gaudinet et al. (Tetrahedron Letters, 1997, 38, 6585-6588) reacted ethyl carboxylate with allyl samarium diiodide to prepare diallyl alcohol, but in this reaction, diiodo The preparation of allyl samarium is complicated and the yield is low

In 2000, Jehyeon Yoo and Kyung Eun Oh et al. (polyhedron, 2000, 19, 549-551) used 2-pyridyl esters as raw materials, under the catalyst of indium, to react with allyl groups in solvent water Halide reaction synthesis of bisallyl alcohol, although the reaction steps are simple, the solvent water is cheap and pollution-free, but the cost of the noble metal indium used is high, the pollution is large, and the reaction yield is low

In this synthesis, catalysts and solvents have certain pollution to the environment, and the yield is not very ideal

In 2007, Kao-Hsien Shen and Chun-Wei Kuo (Tetrahedron letters, 2007, 48, 6348~6351) used various carboxylic acid derivatives as raw materials to react with triallyl aluminum in the solvent ether to synthesize diallyl Alcohols, in this synthesis allyl bromide has very low atom economy and a lot of solvent

In short, these methods have the disadvantages of low yield, cumbersome steps, high cost, need to use a large amount of solvent, and pollute the environment.

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