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A method for preparing 2-(6'-methoxy group-2'-naphthyl) propenol

A technology of methoxynaphthalene and allyl alcohol, which is applied in the preparation of organic compounds, chemical instruments and methods, organic compound/hydride/coordination complex catalysts, etc., can solve the problems of large environmental pollution and achieve environmental pollution Small size, high yield, easy operation

Inactive Publication Date: 2010-06-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the Heck reaction is catalyzed by phosphine ligands and metal palladium, and organic amines are used as bases to react with halogenated aromatic hydrocarbons and olefins. In industrial production, organic amines that are difficult to recover must be used as bases, and organic phosphine complexes The body improves the activity of the reaction, causing great environmental pollution

Method used

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  • A method for preparing 2-(6'-methoxy group-2'-naphthyl) propenol
  • A method for preparing 2-(6'-methoxy group-2'-naphthyl) propenol
  • A method for preparing 2-(6'-methoxy group-2'-naphthyl) propenol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: Prepare 2-(6'-methoxy-2'-naphthyl) allyl alcohol by 2-bromo-6-methoxynaphthalene

[0022] 0.24 g (1 mmol) of 2-bromo-6-methoxynaphthalene, 0.29 g (5 mmol) of allyl alcohol, 0.0012 g (0.005 mmol) of palladium acetate, and 0.3 g of Styrene-DVB (D301R) resin ( 1.5 mmol), 10 ml of dimethyl sulfoxide, placed in a 200 ml three-necked flask, stirred and heated, and reacted at 150° C. for 1 hour. After the reaction, cool, extract with dichloromethane (3 × 50 ml) (i.e. extract 3 times, 50 ml each time, the same below), the extract is dried, concentrated, and separated by column chromatography to obtain the product 2-(6'-methanol Oxygen-2'-naphthyl) allyl alcohol 0.182 g, yield 90%. Melting point 132~133℃; 1 H NMR (CDCl 3 )δppm: 1.76(s, 1H), 3.91(s, 3H), 4.63(s, 2H), 5.41(s, 1H), 5.58(s, 1H), 7.11~7.16(m, 2H), 7.57~7.59 (m, 1H), 7.70 ~ 7.74 (m, 2H), 7.82 (m, 1H); 13 C NMR (CDCl 3 ) δppm: 158.6, 147.8, 134.9, 130.4, 129.5, 127.6, 125.5, 125.3, 119.7, 113.1, 106...

Embodiment 2

[0023] Embodiment 2: Prepare 2-(6'-methoxy-2'-naphthyl) allyl alcohol by 2-iodo-6-methoxynaphthalene

[0024] 0.28 g (1 mmol) of 2-iodo-6-methoxynaphthalene, 0.12 g (2 mmol) of allyl alcohol, 0.0022 g (0.01 mmol) of palladium acetate, and 0.3 g (0.3 g) of Styrene-DVB (D301R) resin ( 1.5 mmol), 100 milliliters of dimethylformamide were placed in a 200 milliliter three-necked flask, stirred and heated, and reacted at 50° C. for 50 hours. After the reaction, it was cooled and extracted with dichloromethane (3×50 ml). The extract was dried, concentrated, and separated by column chromatography to obtain 0.178 g of the product, with a yield of 88%.

Embodiment 3

[0025] Embodiment 3: Prepare 2-(6'-methoxy-2'-naphthyl) allyl alcohol by 2-chloro-6-methoxynaphthalene

[0026] 0.19 g (1 mmol) of 2-chloro-6-methoxynaphthalene, 0.058 g (1.0 mmol) of allyl alcohol, 0.0012 g (0.005 mole) of palladium acetate, and 0.4 g (2 millimoles), 50 milliliters of 1-methylpyrrolidone were placed in a 200 milliliter three-neck flask, stirred and heated, and reacted at 150° C. for 1 hour. After the reaction, it was extracted with dichloromethane (3×50 ml), the extract was dried, concentrated, and separated by column chromatography to obtain 0.125 g of the product, with a yield of 62%.

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Abstract

The invention provides a method for preparing 2-(6'-methoxy-2'-naphthyl) allyl alcohol shown in formula (I). The method comprises: 2-halogenated-6-mthoxynaphthalene and allyl alcohol shown in formula(II) are taken as raw materials and are stirred and reacted for 1 to 50 hours in the non-aprotic polar solvent with the existence of macroporous weak base styrene type anion-exchange resin and palladium acetate catalyst under the temperature between 50 DEG C and 150 DEG C; when the reaction is finished, the reacting liquid is separated and purified to produce the 2-(6'-methoxy-2'- naphthyl) allylalcohol. The preparation method of the invention has a simple preparation process, high yield and easy operation, has the weak base anion-exchange resin capable of being reclaimed and reused, does notuse small molecular organic amine or inorganic base, and has small pollution to the environment.

Description

(1) Technical field [0001] The present invention relates to a kind of preparation method of 2-(6'-methoxy-2'-naphthyl) allyl alcohol, especially a kind of 2- The preparation method of (6'-methoxy-2'-naphthyl) allyl alcohol. (2) Background technology [0002] Naproxen (Naproxen) is a non-steroidal anti-inflammatory, antipyretic and analgesic drug, which has a broad demand market at home and abroad. 2-(6'-methoxy-2'-naphthyl)allyl alcohol is an important intermediate of Naproxen medicine. This was studied by Dustin K. James et al. in US Pat. No. 5,286,902. However, in the reported synthetic route, starting from 2-methoxy-6-isopropylnaphthalene, in a high-temperature tubular reactor, after dehydrogenation with a dehydrogenation catalyst to generate an allylnaphthalene compound, after selenium dioxide Made by oxidation. With this synthetic method, the operation is complicated, the reaction conditions are harsh, the selenium dioxide oxidant used is highly toxic, and the sourc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/23C07C41/30B01J31/08B01J31/04
Inventor 裴文董志刚沈忱吴香梅
Owner ZHEJIANG UNIV OF TECH