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Preparation method of alpha-naphthol compound

A compound, naphthol technology, applied in pharmaceutical and chemical intermediates and related chemical fields, can solve problems such as complex starting materials, harsh reaction conditions, and application restrictions, and achieve the effect of easy-to-obtain, simple raw materials, and easy operation

Active Publication Date: 2015-04-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the currently known methods of preparing α-naphthols with copper as a catalyst re

Method used

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  • Preparation method of alpha-naphthol compound
  • Preparation method of alpha-naphthol compound
  • Preparation method of alpha-naphthol compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0039] Example 1: Synthesis of 3-(2-bromophenyl)naphthalen-1-ol(1a)

[0040]

[0041] In a 25mL reactor, add potassium tert-butoxide (0.112g, 1mmol) and copper acetate (0.010g, 0.050mmol). After nitrogen replacement for 3 times, add 0.40mL of anhydrous tetrahydrofuran under nitrogen protection, and add the adjacent Bromoacetophenone (0.198g, 1mmol), stirred at 30°C for 5h, column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether: ethyl acetate = 20:1) to obtain 3-(2-bromophenyl)naphthalen -1-ol0.119g, the yield is 80%. Pale yellow oil; IR(neat)ν3396,3054,1702,1599,1257,1019,911,849,758,531cm -1 ; 1 H-NMR (400MHz, CDCl 3 )δ5.96(s,1H), 6.78(s,1H), 7.07–7.11(m,1H), 7.20–7.25(m,2H), 7.37(d,J=5.2Hz,1H),7.42(dd ,J=8.0,4.0Hz,2H),7.59(d,J=8.0Hz,1H),7.73-7.76(m,1H); 13 C-NMR (100MHz, CDCl 3 )δ110.9,121.4,121.8,122.8,123.9,125.9,127.1,127.6,128.2,129.0,131.6,133.3,134.5,139.0,142.4,150.9; HRMS(EI)calcd for C 16 H 21 BrO:297.9993[M] + ;Found:298.0000.

Example Embodiment

[0042] Example 2: Synthesis of 3-(2-bromo-4-methoxyphenyl)-6-methoxynaphthalen-1-ol(2a)

[0043]

[0044] In a 25mL reactor, add sodium tert-butoxide (1.920g, 20mmol) and cuprous oxide (0.016g, 0.100mmol). After nitrogen replacement for 3 times, add anhydrous N,N-dimethylformate under nitrogen protection Amide 3.40mL, add 4-methoxy-2-bromoacetophenone (0.228g, 1mmol) with stirring, stir at 0℃ for 5h, column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether: ethyl acetate Ester=20:1) to obtain 0.116 g of 3-(2-bromo-4-methoxyphenyl)-6-methoxynaphthalen-1-ol with a yield of 65%. Mp105.0–105.2℃; IR(neat)ν3424,1634,1605,1394,1220,1024,813,574cm -1 ; 1 H-NMR(d 6 -DMSO,400MHz)δ3.83(s,3H), 3.86(s,3H), 6.75(s,1H), 7.04(dd,J=8.4,2.0Hz,1H), 7.12(dd,J=9.2, 2.0Hz, 1H), 7.20 (s, 1H), 7.26 (d, J = 1.6 Hz, 1H), 7.34 (dd, J = 13.2, 5.3 Hz, 2H), 8.07 (d, J = 8.8 Hz, 1H) 10.20(s,1H); 13 C-NMR(d 6 -DMSO,100MHz)δ55.6,56.1,106.5,108.5,114.3,117.6,118.4,118.5,119.3,122.5,1...

Example Embodiment

[0045] Example 3: Synthesis of 3-(2-bromo-4-fluorophenyl)-6-fluoronaphthalen-1-ol(3a)

[0046]

[0047] In a 25mL reactor, add sodium tert-butoxide (1.920g, 20mmol) and cuprous oxide (0.032g, 0.200mmol). After nitrogen replacement for 3 times, add anhydrous N,N-dimethylformaldehyde under nitrogen protection. Amide 3.40mL, add 4-fluoro-2-bromoacetophenone (0.217g, 1mmol) under stirring, stir at 0°C for 5h, column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether: ethyl acetate = 20:1) 0.104 g of 3-(2-bromo-4-fluorophenyl)-6-fluoronaphthalen-1-ol was obtained, and the yield was 62%. Mp99.0-99.4℃; IR(neat)ν3073,1581,1489,1397,1025,859,820,759cm -1 ; 1 H-NMR(d 6 -DMSO,400MHz)δ6.59(s,1H), 6.94-7.02(m,3H), 7.09-7.13(m,1H), 7.25-7.31(m,2H), 7.90-7.94(m,1H), 10.27(s,1H); 13 C-NMR(d 6 -DMSO,100MHz)δ109.6,111.1(d,J C-F =20.4Hz),115.2,115.5(d,J C-F =8.2Hz),118.7(d,J C-F =4.9Hz), 120.3(d, J C-F =24.2Hz),121.5,122.5(d,J C-F =9.7Hz),125.5(d,J C-F =9.2Hz...

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Abstract

The invention belongs to the field of medical and chemical intermediates and related chemical technology, and relates to a preparation method of an alpha-naphthol compound. According to the preparation method, 2'-chloroacetophenone and a derivative of 2'-chloroacetophenone are taken as the raw materials and perform a self-condensation reaction in an organic solvent under the actions of a copper catalyst and alkali so as to obtain the alpha-naphthol compound. The preparation method of the alpha-naphthol compound has the advantages as follows: the reaction steps are few, the raw materials are simple and easy to obtain, the cost of the catalyst is low, the reaction conditions are mild, and the operation is convenient. The alpha-naphthol compound is a type of important skeletal structure and has quite wide application in the field of pharmaceutical synthesis, and therefore, the preparation method of the alpha-naphthol compound has greater use value as well as social and economic benefits.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and relates to a preparation method of α-naphthol compounds. Background technique [0002] α-Naphthol compounds are widely used in many aspects of the chemical field. As a skeleton structure, they often appear in molecular structures closely related to people's daily necessities, such as drugs, agricultural chemicals, pigments, and optical materials, and have broad market prospects. [0003] There are three traditional methods for synthesizing naphthols. One is the α-naphthalenesulfonic acid alkali fusion method, using naphthalene as the starting material, then sulfonating and alkali melting, and finally obtaining naphthols. This method not only has many synthesis steps , and has defects in the broad spectrum of substrates, the selectivity of the reaction, etc.; the second is the α-naphthylamine hydrolysis method, using α-naphthylamine as ...

Claims

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Application Information

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IPC IPC(8): C07C39/38C07C37/20C07C43/23C07C41/30C07D317/70C07C255/53C07C253/30
CPCC07C37/20C07C41/30C07C253/30C07D317/70C07C39/38C07C43/23C07C255/53
Inventor 于晓强祝培红包明冯秀娟
Owner DALIAN UNIV OF TECH
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