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Butyrolactone-compound production method

A manufacturing method and compound technology are applied in the field of manufacture of butyrolactone compounds to achieve the effect of good yield

Active Publication Date: 2017-08-29
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, as a method for constructing a lactone ring in a polymerizable monomer, a method using a palladium catalyst is known, but these examples still have room for improvement in terms of yield and the like (see Non-Patent Document 3)

Method used

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  • Butyrolactone-compound production method
  • Butyrolactone-compound production method
  • Butyrolactone-compound production method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095]

[0096] To THF (tetrahydrofuran) (100.0g), 4,4'-bis(4-(1,3-dioxolan-2-yl)butoxy)1,1'-biphenyl (10.0g, 23mmol) , hydroxymethyl methacrylate (5.8g, 50mmol) and 5% Pd-C (50% wet; manufactured by Evonik) (2.0g) was dissolved in a mixed solution of stannous chloride dihydrate (15.3g, 68mmol) Then, 0.1N hydrochloric acid aqueous solution (35.7g) was dripped at 64 degreeC over 30 minutes. Thereafter, it was stirred for 24 hours to obtain a reaction mixture containing 4,4'-bis(4-(3-methylenetetrahydrofuran-2(3H)-on-5-yl)butoxy)biphenyl.

[0097] Next, after removing Pd-C by filtration at 50 degreeC, toluene (60.0g) was added to the reaction mixture, and after stirring at 50 degreeC, the hydrochloric acid layer was discarded. Next, the obtained organic layer was dripped at 50 degreeC over 30 minutes to 15.5 wt% potassium hydroxide aqueous solution (75.0g). Then, toluene (50.0g) was further added, and after stirring at 50 degreeC for 10 minutes, the water layer was discarde...

Embodiment 2

[0106]

[0107] To THF (100.0g), 4,4'-bis(4,4-dimethoxybutoxy)-3-fluoro-1,1'-biphenyl (20.0g, 46mmol), hydroxymethylmethacrylate Dissolve stannous chloride dihydrate in a mixed solution of ester (11.7g, 101mmol), 5% Pd-C (50% wet; manufactured by Evonik) (4.0g) and dibutylhydroxytoluene (0.05g, 0.23mmol) After the compound (28.9 g, 128 mmol), 0.1 N hydrochloric acid aqueous solution (35.0 g) was dripped at 64 degreeC over 30 minutes. This was followed by stirring for 24 hours to obtain a reaction mixture comprising 4,4'-bis(3-(3-methylenetetrahydrofuran-2(3H)-on-5-yl)propoxy)-3-fluorobiphenyl .

[0108] Next, toluene (80.0 g) and THF (20.0 g) were added to the reaction mixture, and filtration was performed at 50° C. to remove Pd—C. Then, after stirring at 50 degreeC, the hydrochloric acid layer was discarded. Next, the obtained organic layer was dripped at 50 degreeC over 30 minutes to 15.5 wt% potassium hydroxide aqueous solution (150.0g). Thereafter, the mixture was s...

Embodiment 3

[0112]

[0113] To THF (100.0g), 4,4'-bis(4-(1,3-dioxolan-2-yl)butoxy)-3-fluoro-1,1'-biphenyl (10.0g, 22mmol), hydroxyethyl methacrylate (6.2g, 48mmol) and 5% Pd-C (50% wet; Evonik company make) (2.0g) in the mixed solution of dissolving stannous chloride dihydrate (15.7g, 69 mmol), 0.1N hydrochloric acid aqueous solution (35.7 g) was added dropwise at 64° C. over 30 minutes. This was followed by stirring for 24 hours to give a reaction comprising 4,4'-bis(4-(3-methylenetetrahydrofuran-2(3H)-on-5-yl)butoxy)-3-fluoro-biphenyl mixture. The reaction conversion based on HPLC analysis was 99.3%.

[0114] Regarding the analysis device and analysis conditions of the compound obtained in Example 3, except changing the eluent into acetonitrile / 0.2wt% ammonium acetate aqueous solution (70 / 30 (0-5min)→85 / 15 (10-30min)) [ v / v], the same as in Example 1.

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Abstract

Provided is a novel method for inexpensively producing, in high yield, a polymerizable compound useful for liquid crystal display elements. In this method for producing a compound represented by formula (3) (wherein n represents an integer in the range of 1-10), a compound represented by formula (1) (wherein: n is as described above; PG represents a C1-2 dialkyl acetal group, a 1, 3-dioxane group, or a 1, 3-dioxolane group; and Ar1 represents a biphenylene group or the like) is reacted with a compound represented by formula (2) (wherein R represents a C1-6 alkyl group), under acidic conditions, in the presence of a palladium catalyst and metallic tin or a tin-containing compound.

Description

technical field [0001] The present invention relates to a method for producing a compound having a butyrolactone ring. Background technique [0002] In the liquid crystal display element of the method (also called vertical alignment (VA) method) in which the liquid crystal molecules aligned vertically with respect to the substrate are responded to by an electric field, a step of irradiating ultraviolet rays while applying a voltage to the liquid crystal molecules is included in the manufacturing process. . [0003] For such a liquid crystal display element of a vertical alignment method, it is known to add a photopolymerizable compound to a liquid crystal composition in advance and use it together with a vertical alignment film such as polyimide to apply A technology (PSA (Polymer Sustained Alignment) liquid crystal display) that accelerates the liquid crystal response speed while irradiating ultraviolet rays with a voltage (see Patent Document 1 and Non-Patent Document 1)....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/42C07B61/00
CPCC07B61/00C07D307/42G03F7/0045
Inventor 后藤裕一远藤雅久孙军
Owner NISSAN CHEM IND LTD