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Green synthesis method for substituted ketone

A technology for green synthesis and substitution of ketones, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of difficult to achieve large-scale application, a large number of reaction temperatures, and high catalyst prices, and achieve good popularization and application. Potential, high product recovery, simple product treatment, separation and purification

Inactive Publication Date: 2014-12-24
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these transition metal-catalyzed methods also have many disadvantages: for example, platinum-based transition metals have better catalytic reactions, but the price of these precious metal catalysts is getting higher and higher, making it difficult to achieve large-scale applications; secondly, these Precious metals have the problem of heavy metal residues, which limits the application of products in the fields of medicine, biochemistry and other fields; in addition, many methods reported in the literature need to use a large amount of alkali or high reaction temperature (above 140 degrees); the catalyst is active and easy to deteriorate. The reaction needs to be protected by inert gas or even use equipment such as glove box to complete

Method used

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  • Green synthesis method for substituted ketone
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  • Green synthesis method for substituted ketone

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0019] Preparation of 1,3-Diphenyl-1-acetone from Acetophenone and Benzyl Alcohol

[0020]

[0021] Add acetophenone (2mmol), benzyl alcohol (2.4mmol, 1.2equiv.), NaOH (50mol%), and then add 2mL of toluene as a solvent to a 100mL reaction tube. Seal and heat to 110℃ for 24h in air. 1 HNMR measured the reaction conversion rate of 56%. The product is separated and purified by column chromatography, and the separation yield is 50%. 1 HNMR(500MHz, CDCl 3 ): δ7.94-7.92 (m, 2H), 7.53-7.50 (m, 1H), 7.43-7.40 (m, 2H), 7.29-7.23 (m, 4H), 7.20-7.17 (m, 1H), 3.26 (t,J=7.5Hz,2H),3.05(t,J=7.5Hz,2H). 13 CNMR(125.4MHz, CDCl 3 ): δ199.1, 141.2, 136.7, 132.9, 128.5, 128.4, 128.3, 127.9, 126.0, 40.3, 30.0.

example 2

[0023] Preparation of 1,3-bis(4-methoxyphenyl)-1-acetone from 4-methoxyacetophenone and 4-methoxybenzyl alcohol

[0024]

[0025] Add 4-methoxyacetophenone (2mmol), 4-methoxybenzyl alcohol (2.4mmol, 1.2equiv.), KOH (50mol%) to the 100mL reaction tube, then add 2mL of toluene as a solvent, and seal under air. The reaction was heated to 110°C for 24 hours, and the reaction conversion rate was 95% measured by GC-MS. The product was separated and purified by column chromatography, and the separation yield was 75%. 1 HNMR(300MHz, CDCl 3 ): δ7.94(d,J=8.7Hz,2H), 7.18(d,J=8.4Hz,2H), 6.92(d,J=8.7Hz,2H), 6.85(d,J=8.4Hz,2H ), 3.85(s, 3H), 3.78(s, 3H), 3.22(t, J=7.5Hz, 2H), 3.00(t, J=7.5Hz, 2H). 13 CNMR(125.4MHz, CDCl 3 ): δ197.9, 163.3, 157.8, 133.3, 130.2, 129.8, 129.2, 113.8, 113.6, 55.3, 55.1, 40.2, 29.3. MS(EI): m / z(%) 77(14), 92(7), 107 (7), 108(7), 121(49), 134(12), 135(100), 136(9), 270(29).

example 3

[0027] Preparation of 3-(4-methoxyphenyl)-1-phenyl-1-acetone from acetophenone and 4-methoxybenzyl alcohol

[0028]

[0029] Add acetophenone (2mmol), 4-methoxybenzyl alcohol (2.4mmol, 1.2equiv.), KOH (50mol%) to the 100mL reaction tube, then add 2mL of toluene as a solvent, and heat to 110℃ under air tightly for reaction. At 24h, GC-MS measured the conversion rate of 98%. The product was separated and purified by column chromatography with a separation yield of 68%. 1 HNMR(300MHz, CDCl 3 ): δ7.97(d,J=7.5Hz,2H), 7.57(t,J=7.2Hz,1H), 7.46(t,J=7.5Hz,2H), 7.19(d,J=8.7Hz,2H ), 6.86(d,J=8.7Hz,2H), 3.80(s,3H), 3.28(t,J=7.5Hz,2H), 3.03(t,J=7.5Hz,2H). 13 CNMR(125.4MHz, CDCl 3 ): δ199.4, 158.0, 136.9, 133.3, 133.0, 129.3, 128.6, 128.0, 113.9, 55.3, 40.7, 29.3. MS(EI): m / z(%) 77(32), 91(10), 105(39 ), 108(17), 121(100), 122(10), 135(13), 240(37).

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Abstract

The invention provides a green synthesis method for substituted ketone, i.e., the substituted ketone is synthesized through the reaction of methyl ketone and alcohol in the existence of inert gases or air under an alkaline condition. The method is mild in reaction condition and can be carried out in the existence of the inert gases or air; and a product is simple in treatment, separation and purification and high in recovery rate. The method has the advantages that no transition metal catalysts are needed, primary alcohol which is cheap and easy to obtain is used as an alkylating reagent, water is produced as a unique byproduct, not only is the synthesis cost greatly reduced, but also no transition metal residues remain, and no wastes and pollution are caused, thus the green synthesis method has favorable popularization and application potential.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a green synthesis method for synthesizing substituted ketones by the dehydration α-alkylation reaction of methyl ketones in the presence of primary alcohols as alkylating reagents without transition metal catalysts, that is, to a substituted ketone The green synthesis method. Background technique [0002] The α-alkylation reaction of α-hydrogen-containing methyl ketones is one of the basic methods for forming C-C bonds and preparing substituted ketones in synthetic chemistry. Traditionally, this reaction uses methyl ketone and halogenated hydrocarbons under alkaline conditions, through the formation of enol salt intermediates and halogenated hydrocarbons in a new nuclear substitution reaction, or through the selective reduction of chalcone, Chalcone can be obtained by aldol condensation reaction of methyl ketone, aldehyde and ketone. However, the nucleophilic substitution method requ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/782C07C49/84C07C45/64C07C45/71C07D213/50C07D333/22
Inventor 徐清陈建辉田海雯袁雪勤周崇款
Owner WENZHOU UNIV