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Method for synthesizing polysubstitution 3-phenyl-1-naphthol

A polysubstituted, phenyl technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as difficult preparation, and achieve the effect of easy separation and purification

Active Publication Date: 2010-01-06
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Recently, it has been reported in the literature that 3-siliconyl phenynes undergo a Diels-Alder reaction with substituted furans to generate 4-substituted 1-naphthols (Akai, S.; Ikawa, T.; Takayanagi, S.-I.; Morikawa , Y.; Mohri, S.; Tsubakiyama, M.; Egi, M.; Wada, Y.; Kita, Y. Angew.Chem., Int.Ed.2008, 47, 7673), but its raw materials are not easy to prepare, At the same time, the substituent is limited to the 4-position of 1-naphthol

Method used

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  • Method for synthesizing polysubstitution 3-phenyl-1-naphthol
  • Method for synthesizing polysubstitution 3-phenyl-1-naphthol

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Add diphenylzinc (0.1308 g, 0.6 mmol) to the reaction tube in the glove box, add xylene (3 ml) under nitrogen protection, and place in an oil bath at 140°C. Add 2-methyl-4-phenyl-2,3-butadienoic acid ethyl ester (0.0403 g, 0.2 mmol) in xylene solution (2 ml) to the reaction tube under stirring, and react at 140 degrees Celsius After 0.5 hours, add 1 ml of saturated ammonium chloride solution dropwise to quench the reaction, naturally return to room temperature and drop to zero, extract with ether, wash once with 5% hydrochloric acid, saturated sodium bicarbonate, saturated saline, and anhydrous sodium sulfate dry. Filtration, concentration, and flash column chromatography gave 0.0262 g of 2-methyl-3-phenyl-1-naphthol with a yield of 56%. The product is a white solid:

[0019] m.p.52.1-54.4℃(hexane / ethyl acetate); 1 H NMR (300MHz, CDCl 3 )δ8.17-8.09 (m, 1H), 7.79-7.72 (m, 1H), 7.52-7.32 (m, 8H), 5.24 (s, 1H), 2.27 (s, 3H); 13 C NMR (CDCl 3 , 75MHz) δ148.9, 141.7, 1...

Embodiment 2

[0021] According to the method described in Example 1, the difference is that the substrate and reagent used are: 2-methyl-4,4-diphenyl-2,3-butadienoic acid ethyl ester (0.0570 grams, 0.2 mmol) , diphenylzinc (0.1312 g, 0.6 mmol) to obtain 0.0574 g of 2-methyl-3,4-diphenyl-1-naphthol with a yield of 90%. The product is a white solid:

[0022] m.p.162.3-164.1℃(hexane / ethyl acetate); 1 H NMR (300MHz, CDCl 3 )δ8.23 (d, J = 8.7Hz, 1H), 7.56-7.41 (m, 2H), 7.40-7.28 (m, 1H), 7.25-6.95 (m, 10H), 5.27 (s, 1H), 2.14 (s, 3H); 13 C NMR (CDCl 3 , 75MHz) δ148.0, 140.6, 140.1, 139.5, 131.9, 131.6, 131.5, 130.2, 127.5, 127.4, 126.7, 126.15, 126.09, 125.7, 125.2, 123.2, 120.8, 115.3, 13.8 m / z; MS(EI) (%)311(M + +1, 25.05), 310 (M + , 100); IR(KBr, cm -1 )3550, 3444, 3057, 3028, 2924, 2856, 1592, 1497, 1442, 1374, 1289, 1212, 1160, 1097, 1027; Anal. Calcd for C 23 h 18 O: C 89.00, H 5.85, Found: C 88.97, H 5.85.

Embodiment 3

[0024] According to the method described in Example 1, the difference is that the substrate and reagent used are: ethyl 2-propyl-4,4-diphenyl-2,3-butadienoate (0.0618 g, 0.2 mmol) , diphenylzinc (0.1320 g, 0.6 mmol) to obtain 0.0618 g of 2-propyl-3,4-diphenyl-1-naphthol with a yield of 91%. The product is a white solid:

[0025] m.p.140.7-142.8℃(hexane / ethyl acetate); 1 H NMR (300MHz, CDCl 3 )δ8.24 (d, J = 8.1Hz, 1H), 7.54-7.40 (m, 2H), 7.39-7.30 (m, 1H), 7.25-6.98 (m, 10H), 5.33 (s, 1H), 2.59 -2.46(m, 2H), 1.56-1.42(m, 2H), 0.83(t, J=7.2Hz, 3H); 13 C NMR (CDCl 3 , 75MHz) δ148.0, 140.3, 140.1, 139.6, 132.0, 131.8, 131.4, 130.3, 127.3, 127.2, 126.8, 126.1, 126.0, 125.8, 125.1, 123.5, 120.9, 120.5, 29.9, 24.1; MS (E )m / z(%)339(M + +1, 26.63), 338 (M +, 100); IR(KBr, cm -1 )3581, 3417, 2959, 1588, 1498, 1445, 1380, 1203, 1160, 1100, 1029; Anal. Calcd for C 25 h 22 O: C 88.72, H 6.55, Found: C 88.79, H 6.54.

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Abstract

The invention discloses a method for synthesizing polysubstitution 3-phenyl-1-naphthol. At a temperature of 140 DEG C, dimethylbenzene is taken as a solvent, diphenylzinc agent and 2,3-linked allenoates carries out 1,4-addition reaction and intramolecular cyclization reaction to obtain a series of polysubstitution 3-phenyl-1-naphthol compounds. The reaction does not need catalysts, and the synthesis method has simple operation easily obtained raw materials and reagents, and easily separated and purified product, can introduce three substitution groups simultaneously to 1-naphthol, and is suitable for synthesizing various types of polysubstitution 3-phenyl-1-naphthol.

Description

technical field [0001] The invention relates to a method for substituting 1-naphthol with 3-phenyl. Background technique [0002] Naphthol and its derivatives are a class of extremely important compounds that can be used in the synthesis of dyes, antioxidants, preservatives, pesticides, rubber, paints, etc., and are widely used in chemical production. It is also used to prepare chiral ligands and polyaromatic compounds, and is an important intermediate in organic synthesis. It is also the basic skeleton of many natural products. However, in the synthesis of naphthol compounds reported in the past, there has been no systematic synthesis method for multi-substituted 1-naphthols. Recently, it has been reported in the literature that 3-silyl phenylenes react with substituted furans to generate 1-naphthols (Akai, S.; Ikawa, T.; Takayanagi, S.-I.; Morikawa , Y.; Mohri, S.; Tsubakiyama, M.; Egi, M.; Wada, Y.; Kita, Y. Angew.Chem., Int.Ed.2008, 47, 7673), but its raw materials ar...

Claims

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Application Information

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IPC IPC(8): C07C37/00C07C39/225
Inventor 麻生明柴国璧陆展傅春玲
Owner ZHEJIANG UNIV
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