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Process for producing tetrahydropyran-4-carboxylic acid compound

A technology of carboxylic acid compound and tetrahydropyran, which is applied in the field of preparation method of tetrahydropyran-4-carboxylic acid compound, can solve the problem of high reaction temperature, can not become tetrahydropyran-4-carboxamide compound, and can not be used as a tetrahydropyran-4-carboxamide compound. low rate issues

Inactive Publication Date: 2007-10-24
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned method has the following problems: a high reaction temperature is required, and the yield is low, making it unsatisfactory as an industrial production method of tetrahydropyran-4-carboxylic acid
However, there are the following problems in this method: a large amount of tetra-n-butylphosphine bromide is required, the reaction temperature is high, and the yield of the target substance is low, etc.
However, there is no detailed description of the production method and the description of the yield etc. in this method, so it cannot be used as a reference for an industrial production method of tetrahydropyran-4-carboxamide compound.

Method used

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  • Process for producing tetrahydropyran-4-carboxylic acid compound
  • Process for producing tetrahydropyran-4-carboxylic acid compound
  • Process for producing tetrahydropyran-4-carboxylic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1 (the synthesis of tetrahydropyran-4-carboxylic acid)

[0074]Add 0.85 g (5.0 mmol) of methyl 4-cyanotetrahydropyran-4-carboxylate and 3.5 ml (21 mmol) of 6 mol / l hydrochloric acid in a glass vessel with a stirring device, a thermometer and an inner volume of 20 ml, The reaction was carried out at 100° C. for 7 hours while stirring. After completion of the reaction, the reaction liquid was analyzed (internal standard method by gas chromatography), and 0.51 g of tetrahydropyran-4-carboxylic acid was produced (reaction yield: 78%).

Embodiment 2

[0075] Embodiment 2 (tetrahydropyran-4-carboxylic acid synthesis)

[0076] Add 1.0g (6.5mmol) of 4-cyanotetrahydropyran-4-carboxylic acid and 10ml (60mmol) of 6mol / l hydrochloric acid to a glass container with a stirring device, a thermometer and an inner volume of 20ml, and stir The reaction was carried out at 100°C for 9 hours. After completion of the reaction, the reaction liquid was analyzed (internal standard method by gas chromatography), and as a result, 0.74 g of tetrahydropyran-4-carboxylic acid was produced (reaction yield: 88%).

Embodiment 3

[0077] Embodiment 3 (the synthesis of tetrahydropyran-4-carboxylic acid)

[0078] Add 0.5 g (3.2 mmol) 4-cyanotetrahydropyran-4-carboxylic acid, 0.5 g (3.0 mmol) 4-cyanotetrahydro Methyl pyran-4-carboxylate and 10ml (60mmol) of 6mol / l hydrochloric acid were reacted at 100°C for 9 hours while stirring. After completion of the reaction, the reaction liquid was analyzed (internal standard method by gas chromatography), and as a result, 0.68 g of tetrahydropyran-4-carboxylic acid was produced (reaction yield: 84%).

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Abstract

A process for producing tetrahydropyran-4-carboxylic acid of the formula: (1) characterized by hydrolytic reaction, in the presence of an acid, of a 4-cyanotetrahydropyran-4-carboxylic acid compound of the formula: (2) wherein R is a hydrogen atom or hydrocarbon group. Further, there is provided a process for producing a tetrahydropyran-4-carboxylic acid ester, characterized by reaction, in the presence of an acid, between tetrahydropyran-4-carboxylic acid of the formula (1) and an alcohol. Still further, there is provided a process for producing a tetrahydropyran-4-carboxamide, characterized by reaction between tetrahydropyran-4-carboxylic acid of the formula (1) and a halogenating agent to thereby produce a tetrahydropyran-4-carboxylic halide, followed by reaction with an amine compound.

Description

technical field [0001] The present invention relates to the production of tetrahydropyran-4-carboxylic acid, tetrahydropyran-4-carboxylate, tetrahydro Methods for Pyran-4-Carboxyl Halides and Tetrahydropyran-4-Carboxamides. Tetrahydropyran-4-carboxylic acid compounds are compounds useful as raw materials for pharmaceuticals, agricultural chemicals, etc., and as synthetic intermediates. Background technique [0002] Conventionally, as a method for producing tetrahydropyran-4-carboxylic acid, it is known, for example, to heat tetrahydropyran-4,4-dicarboxylic acid to 185°C to obtain tetrahydropyran-4 in an isolated yield of 64%. - A carboxylic acid method (see, for example, Patent Document 1). However, the above method has problems in that a high reaction temperature is required and the yield is low, making it unsatisfactory as an industrial production method of tetrahydropyran-4-carboxylic acid. [0003] In addition, as a method for producing tetrahydropyran-4-carboxylate, ...

Claims

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Application Information

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IPC IPC(8): C07D309/08
Inventor 西野繁荣弘津健二岛秀好原田崇司中村卓岩本圭司
Owner UBE IND LTD