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Preparation method of 4-vinylphenol compound

A vinylphenol and compound technology, applied in the field of preparation of 4-vinylphenol compounds, can solve problems such as limited universality of substrates, and achieve the effects of stable yield, improved production efficiency and short reaction time

Pending Publication Date: 2022-01-04
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

In the synthetic method of 4-vinylphenol compounds, the decarboxylation reaction of carboxylic acid is its main preparation approach, but because the existence of hydroxyl group is very easy to produce polymerization, in order to solve this problem, there are some chemical reports (Tetrahedron, 2007,63,960 ; Tetrahedron Lett., 2005, 46, 6893; Tetrahedron, 2007, 63, 9663; ACS Sustain. Chem. Eng., 2018, 6, 7232; Tetrahedron, 2007, 63, 7640; .Org.Chem., 1966, 31, 2712; Green Chem., 2014, 16, 3089), biology (ACS Sustain.Chem.Eng., 2019, 7, 16364; J.Sci.Food Agr., 2012, 92, 610 ; Chem.Pharm.Bull., 2001, 49, 639; Tetrahedron lett., 1999, 40, 6595; , 23,261; Appl.Environ.Microb., 1993,59,2244) synthetic methods, however, the substrate universality of these methods is limited, as only the synthesis of 4-vinylphenol substituted by electron-donating groups has been reported

Method used

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  • Preparation method of 4-vinylphenol compound
  • Preparation method of 4-vinylphenol compound
  • Preparation method of 4-vinylphenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: a kind of preparation method of 4-vinylphenol compound:

[0024] Add 0.2mmol of p-hydroxycinnamic acid and 1mL of solvent DMF to the pressure-resistant reaction bottle, heat and stir in an oil bath at 200°C for 30 minutes; after the reaction, extract the reaction solution with ethyl acetate three times, and wash the organic layer with water and saturated sodium chloride solution in sequence , then dry the washed organic layer with anhydrous sodium sulfate, filter, and the residue after the filtrate is concentrated under reduced pressure is subjected to silica gel column chromatography (V 石油醚 / V 乙酸乙酯 =5:1) separation and purification to obtain 4-vinylphenol compound I-1 with a yield of 89%.

[0025] The nuclear magnetic resonance (NMR) of the prepared 4-vinylphenol compound (I-1) 1 H NMR and 13 C NMR) detection data are: 1 H NMR (600MHz, DMSO-d6) δ7.29–7.23 (m, 2H), 6.72 (d, J = 8.5Hz, 2H), 6.60 (dd, J = 17.6, 10.9Hz, 1H), 5.57 (dd, J=17.6,0.9Hz,1H),5....

Embodiment 2

[0026] Embodiment 2: a kind of preparation method of 4-vinylphenol compound:

[0027] Add 0.2mmol of 3,4-dihydroxycinnamic acid and 1mL of solvent DMF to the pressure-resistant reaction flask, heat and stir in an oil bath at 200°C for 30min; The organic layer was washed with solution, and the organic layer after washing was dried with anhydrous sodium sulfate, filtered, and the residue after the filtrate was concentrated under reduced pressure was subjected to silica gel column chromatography (V 石油醚 / V 乙酸乙酯 =5:1) separation and purification to obtain 4-vinylphenol compound I-2 with a yield of 87%.

[0028] The nuclear magnetic resonance (NMR) of the prepared 4-vinylphenol compound (I-2) 1 H NMR and 13 C NMR) detection data are: 1 H NMR (600MHz, CD 3 OD) δ6.94(d, J=1.8Hz, 1H), 6.78(dd, J=8.1, 1.8Hz, 1H), 6.75(d, J=8.1Hz, 1H), 6.61(dd, J=17.6, 10.9Hz,1H),5.56(dd,J=17.6,0.9Hz,1H),5.06(dd,J=10.9,0.8Hz,1H). 13 C NMR (151MHz, CD 3 OD)δ145.16, 144.98, 136.75, 130.03, 118.31, ...

Embodiment 3

[0029]Embodiment 3: a kind of preparation method of 4-vinylphenol compound:

[0030] Add 0.2mmol of 3-methoxy-4-hydroxycinnamic acid and 1mL of solvent DMF to a pressure-resistant reaction flask, heat and stir in an oil bath at 200°C for 30min; Wash the organic layer with sodium chloride solution, then dry the washed organic layer with anhydrous sodium sulfate, filter, and the residue after the filtrate is concentrated under reduced pressure is subjected to silica gel column chromatography (V 石油醚 / V 乙酸乙酯 =5:1) separation and purification to obtain 4-vinylphenol compound I-3 with a yield of 94%.

[0031] The nuclear magnetic resonance (NMR) of the prepared 4-vinylphenol compound (I-3) 1 H NMR and 13 C NMR) detection data are: 1 H NMR (600MHz, CDCl 3 )δ6.95–6.91(m,2H),6.87(d,J=8.1Hz,1H),6.64(dd,J=17.5,10.8Hz,1H),5.65(s,1H),5.59(d,J =17.5Hz,1H),5.13(d,J=10.9Hz,1H),3.91(s,3H). 13 CNMR (151MHz, CDCl 3 )δ146.59, 145.64, 136.63, 130.28, 120.08, 114.35, 111.47, 108.01, 55.89. ...

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Abstract

The invention provides a preparation method of a 4-vinylphenol compound, which specifically comprises the following steps: preparing according to the following reaction formula: adding substituted p-hydroxycinnamic acid and a solvent N, N-dimethylformamide into a pressure-resistant reaction flask, heating and stirring to react for 30 minutes, and separating and purifying after the reaction is finished to obtain the 4-vinylphenol compound. According to the preparation method, DMF is used as a solvent, a catalyst is not needed, the reaction time is short (30 min), substrate universality is good, polymerization reaction is avoided, operation is easy, the production period and cost are greatly reduced, the average yield of the target compound is stable and can reach 96% to the maximum, a new method is provided for synthesis of the 4-vinylphenol compound, and a foundation is laid for large-scale production of products and improvement of production efficiency.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of 4-vinylphenol compounds. Background technique [0002] In organic synthesis, 4-vinylphenols provide starting materials for the direct conversion of C–H bonds into various valuable C–C and C-heteroatom bonds. They are used to synthesize bioactive compounds (Tetrahedron, 2006, 62, 4214; Bioorg.Med.Chem., 1994, 2, 553), resins, elastomers, adhesives, coatings and electronic materials (React.Funct.Polym. , 1998, 37, 39). Some 4-vinylphenols with different substituents exhibit various biological activities, such as antioxidant, antitumor, antibacterial and antimutagenic activities (Biochim.Biophys.Acta., 1984,789,111; Phytochemistry, 1996,42,1321; Agric. Food Chem., 2004, 52, 4380; Eur. Food Technol., 2003, 217, 110; Agric. Food Chem., 2006, 54, 6054) and so on. In the synthetic method of 4-vinylphenol compounds, the decarboxylation re...

Claims

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Application Information

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IPC IPC(8): C07C37/50C07C39/06C07C39/08C07C39/27C07C39/28C07C41/18C07C43/23C07C201/12C07C205/22
CPCC07C37/50C07C41/18C07C201/12C07C37/002C07C39/06C07C39/08C07C39/27C07C39/28C07C43/23C07C205/22
Inventor 杨小生杨礼寿杨倩王恩花邓廷飞李良群陈发菊曹家辅谭云飞
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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