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Method for producing alcohols having fluorene skeleton

A manufacturing method and technology of alcohols, applied in ether preparation, organic chemistry, ester reaction to prepare ethers, etc., can solve problems such as unknown manufacturing methods of alcohols, and achieve the effect of reducing the quantity

Active Publication Date: 2019-11-15
TAOKA CHEM COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] On the other hand, the production method of alcohols represented by the above formula (1) is almost unknown, and only the following two synthetic routes are known

Method used

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  • Method for producing alcohols having fluorene skeleton
  • Method for producing alcohols having fluorene skeleton
  • Method for producing alcohols having fluorene skeleton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0135] Add 30.0 g (0.17 mol) of 9-fluorenone, 57.6 g (0.40 mol) of 2-naphthol, and 1.79 g (0.008 mol), toluene 45.0g, γ-butyrolactone 14.8g and phosphotungstic acid 0.8g, decompressed to 49.3kPa, then raised the temperature to 100°C, stirred at the same temperature for 7 hours, and confirmed 9-fluorenone by HPLC The residual rate is less than 0.2%.

[0136] Next, 0.9 g of a 24% aqueous sodium hydroxide solution (hereinafter also referred to as caustic water) was added to the obtained reaction liquid to neutralize phosphotungstic acid, and then the temperature was raised to 120° C. to distill water.

[0137] Then, 1.2 g of potassium carbonate, 36.6 g of ethylene carbonate, and 1.5 g of toluene were added to the reaction solution, the temperature was raised to 110° C., and then stirred at the same temperature for 13 hours. It was confirmed by HPLC that the formula (2-1) represented The disappearance of bis-naphthol compounds.

[0138] After completion of the reaction, 7.5 g of...

Embodiment 2

[0144] Add 30.0 g (0.17 mol) of 9-fluorenone, 57.6 g (0.40 mol) of 2-naphthol, and 1.79 g (0.008 mol), toluene 30.0g, ethyl acetate 30.0g and phosphotungstic acid 0.8g, decompressed to 56.7kPa, then raised the temperature to 100°C, stirred at the same temperature for 4 hours, and confirmed the residue of 9-fluorenone by HPLC rate of 0.2% or less.

[0145] Next, 0.9 g of 24% caustic water was added to the obtained reaction liquid to neutralize phosphotungstic acid, and then the temperature was raised to 120° C. to distill water.

[0146] Then, 1.2 g of potassium carbonate, 36.6 g of ethylene carbonate, and 1.5 g of toluene were added to the reaction liquid, the temperature was raised to 110° C., and then stirred at the same temperature for 16 hours, and the formula (2-1) represented by the above-mentioned formula (2-1) was confirmed by HPLC. Disappearance of bis-naphthol compounds.

[0147] After completion of the reaction, 7.5 g of water and 26.3 g of 24% caustic water were ...

Embodiment 3

[0151] Except having changed the ethyl acetate in Example 2 into butyl acetate, it carried out similarly, and obtained the alcohol compound represented by said formula (1-1). The yield, yield and purity of the obtained alcohol compound represented by the above formula (1-1) are shown below.

[0152] Weight of obtained crystals: 80.9 g (yield: 90.2%)

[0153] HPLC purity: 94.6%

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Abstract

Provided is a method for producing alcohols represented by formula (1), which sequentially comprises in the following order: a step (i) for obtaining a bisnaphthol compound represented by formula (2)by reacting 9-fluorenone and naphthol with each other in the presence of a solid acid; and a step (ii) for reacting the bisnaphthol compound represented by formula (2) with ethylene carbonate withouttaking out the bisnaphthol compound from the reaction system. (In the formulae, n1 and n2 may be the same or different, and each represents an integer of 1 or more.)

Description

technical field [0001] The invention relates to a method for producing alcohols with a fluorene skeleton. Background technique [0002] Alcohols represented by the following formula (1) are prepared as raw materials for optical resins because resins produced from the alcohols and their derivatives have excellent optical properties such as light transmittance and refractive index, and thermal properties such as heat resistance. Attention [For example, International Publication No. 2016 / 047766 (Patent Document 1), International Publication No. 2016 / 147847 (Patent Document 2), Japanese Patent Application Publication No. 2011-168723 (Patent Document 3), Japanese Patent Application Publication No. 2011-068624 Gazette (Patent Document 4)]. [0003] [chemical formula 1] [0004] [0005] (where, n 1 and n 2 Each is the same or different and represents an integer of 1 or more. ) [0006] On the other hand, the production method of alcohols represented by the above-mentioned...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/23
CPCC07C41/16C07C43/23
Inventor 半田康春松浦隆河井秀树
Owner TAOKA CHEM COMPANY
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