Synthesis of benzoxanthene derivatives by aqueous phase catalysis of ionic liquid
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A technology of benzoxanthene and ionic liquid, which is applied in the field of synthesis of benzoxanthene derivatives catalyzed by ionic liquid in water phase, can solve the problems of lack of large-scale industrial application, catalysts that cannot be recycled, and complex catalyst preparation process, etc. problem, to achieve the effect of water stability, convenient preparation and high activity
Inactive Publication Date: 2013-01-02
YANCHENG TEACHERS UNIV
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These methods have one or more of the following disadvantages: the preparation process of the catalyst is complicated; the catalyst cannot be recycled; the equipment is severely corroded; the operation process is complicated; it can only be suitable for laboratories or small-scale operations, and does not have large-scale industrial applications Wait
In recent years, the application of ionic liquids in organic synthesis is very active, but as a catalyst to synthesize benzoxa[c]anthracene derivatives using α-naphthol, aromatic aldehydes, and 1,3-cyclohexanedione derivatives as raw materials. see the report
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Embodiment 1
[0024] In a 25mL round bottom flask, add 10mmol (1.061g) benzaldehyde, 10mmol (1.121g) 1,3-cyclohexanedione, 10mmol (1.442g) α-naphthol, 0.5mmol catalyst, 4mL water in sequence, Stir and reflux at 100°C for 1 hour under normal pressure, cool, filter and wash with cold water, and recrystallize from 95% ethanol to obtain pure 7-phenyl-benzoxa[c]anthracene with a yield of 85%.
Embodiment 2
[0026] In a 25mL round bottom flask, add 10mmol (1.061g) benzaldehyde, 10mmol (1.402g) 5,5-dimethyl-1,3-cyclohexanedione, 10mmol (1.442g) α-naphthol, 0.5 mmol of catalyst, 5mL of water, mixed and stirred at 100°C under normal pressure for 1.5 hours, cooled, filtered and washed with cold water, recrystallized from 95% ethanol to obtain 10,10-dimethyl-7-phenyl-benzoxa[ c] The pure product of anthracene, the yield is 85%.
Embodiment 3
[0028] In a 25mL round bottom flask, add 10mmol (1.221g) 4-hydroxybenzaldehyde, 10mmol (1.402g) 5,5-dimethyl-1,3-cyclohexanedione, 10mmol (1.442g) α-naphthalene Phenol, 0.8mmol of catalyst, 5mL of water, mixed and stirred at 100°C under normal pressure for 2.5 hours under reflux, cooled, filtered and washed with cold water, recrystallized from 95% ethanol to obtain 10,10-dimethyl-7-(4-hydroxy- The pure product of phenyl)benzoxa[c]anthracene, the yield is 83%.
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Abstract
The invention discloses a new method for synthesis of benzoxanthene derivatives by aqueous phase catalysis of ionic liquid. The catalyst is alkaline functionalized ionic liquid; the raw materials are alpha-naphthol, aromatic aldehyde, and 1,3-cyclohexanedione derivatives; water is used as a reaction medium; and the benzoxanthene derivatives are obtained by reaction under the action of the catalyst. Compared with the prior art, the invention has the following advantages that: (1) the alkaline functionalized ionic liquid is adopted, the raw materials are wide in sources, the preparation is convenient; the catalyst is high in activity, few in using amount, stable and not inactive when used in water; (2) the aqueous solution containing the ionic liquid catalyst can be recycled, and is environment friendly; (3) water is used instead of organic solvents, which has dual benefits of environment and economy, and the method is a high-efficient and environment-friendly method for synthesis of benzoxanthene derivatives, and facilitates large-scale industrial production.
Description
a technical field [0001] The invention relates to a new synthesis method of benzoxanthene derivatives catalyzed by ionic liquid water phase, and belongs to the technical field of chemical material preparation. The method is suitable for the occasion of synthesizing benzoxanthene derivatives by using α-naphthol, aromatic aldehyde and 1,3-cyclohexanedione derivatives as raw materials. Two background technology [0002] Benzoxanthracene compounds are an important class of pharmaceutical intermediates. The skeleton structure of anthracene widely exists in many natural compounds with biological activity, and different structures exhibit different properties, and different spatial structures exhibit different biological activities. . Benzoxanthene is an intermediate in the synthesis of various drugs, and it has been found to have antitumor, antiviral, antibacterial, anti-inflammatory and anti-implantation activities; in addition, benzoxanthene is used as a photosensitizing dye in...
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