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Green synthesis method for substituted ketone

A green synthesis and ketone-replacing technology, which is applied in chemical instruments and methods, carbon-based compound preparation, organic compound preparation, etc., can solve problems such as difficult to achieve large-scale application, limited product application, high catalyst price, etc., and achieve good promotion and application potential, ease of operation, and high product recovery

Inactive Publication Date: 2013-08-07
WENZHOU UNIVERSITY
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  • Description
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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
  • Green synthesis method for substituted ketone
  • Green synthesis method for substituted ketone

Examples

Experimental program
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Effect test

example 1

[0019] Preparation of 1,3-diphenyl-1-propanone from acetophenone and benzyl alcohol

[0020]

[0021] Add acetophenone (2mmol), benzyl alcohol (2.4mmol, 1.2equiv.), NaOH (50mol%) in turn into a 100mL reaction tube, and then add 2mL toluene as a solvent, and heat it to 110°C under the air for 24h. 1 HNMR records that the reaction conversion rate is 56%. The product was separated and purified by column chromatography, and the separation yield was 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-propanone from 4-methoxyacetophenone and 4-methoxybenzyl alcohol

[0024]

[0025] Add 4-methoxyacetophenone (2mmol), 4-methoxybenzyl alcohol (2.4mmol, 1.2equiv.), KOH (50mol%) in turn into a 100mL reaction tube, then add 2mL toluene as a solvent, and seal it under air Heating to 110°C for 24h, the reaction conversion rate was 95% as 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-propanone from acetophenone and 4-methoxybenzyl alcohol

[0028]

[0029] Add acetophenone (2mmol), 4-methoxybenzyl alcohol (2.4mmol, 1.2equiv.), KOH (50mol%) in turn into a 100mL reaction tube, then add 2mL toluene as a solvent, seal and heat to 110°C under air to react After 24 hours, the conversion rate of the reaction was 98% as measured by GC-MS. The product was separated and purified by column chromatography, and the separation yield was 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 through the dehydration α-alkylation reaction of methyl ketones in the absence of transition metal catalysts in the presence of primary alcohols as alkylating reagents, that is, to a substituted ketones green synthesis method. Background technique [0002] The α-alkylation reaction of α-hydrogen-containing methyl ketones is one of the basic methods in synthetic chemistry to form C-C bonds and prepare substituted ketones. Traditionally, this reaction has been achieved using methyl ketones with halohydrocarbons under basic conditions, via neonuclear substitution reactions of the formed enolate intermediates with halohydrocarbons, or via selective reduction of chalcones, Chalcones can be obtained by the aldol condensation reaction of methyl ketones with aldehydes and ketones. However, the nucleophilic substitution method...

Claims

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Application Information

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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 UNIVERSITY
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