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Synthetic method of 2-methyl-1-(4'-methylthiophenyl)-2-morpholinyl-1-acetone

The technology of a methylthiophenyl group and a synthesis method, which is applied in the field of organic chemical synthesis, can solve problems such as potential safety hazards in downstream use of photoinitiators, and achieve the effects of low cost of raw materials, simple and easily available raw materials, and strong competitive advantages.

Inactive Publication Date: 2014-04-16
ZHEJIANG QIMING PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method improves the yield of the product and the utilization rate of bromine, it needs to use highly toxic thioanisole and bromine, which brings a greater safety hazard to the downstream use of photoinitiators

Method used

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  • Synthetic method of 2-methyl-1-(4'-methylthiophenyl)-2-morpholinyl-1-acetone
  • Synthetic method of 2-methyl-1-(4'-methylthiophenyl)-2-morpholinyl-1-acetone
  • Synthetic method of 2-methyl-1-(4'-methylthiophenyl)-2-morpholinyl-1-acetone

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Experimental program
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Embodiment 1

[0049] The preparation of embodiment 11-(4'-chlorophenyl)-2-methyl-1,2-propylene oxide

[0050] In a 2000ml four-neck flask, first add 644g of p-chlorobenzyl chloride, then add 348g (5.6mol) of dimethyl sulfide, 300g of water, heat and reflux for 12 hours, the reaction temperature is 50-55°C, when the reaction liquid becomes homogeneous After the reaction is over, cool down to 38-40°C, add 232g (4mol) of acetone, then add dropwise 915g of 35% liquid caustic soda, slowly heat to 50°C after the dropwise addition, and take a sample to detect the acetone content after the reaction for 10 hours. Change, stop the reaction, lower the temperature to 20°C, let stand to separate the water layer, the organic layer is firstly distilled at normal pressure to recover acetone and dimethyl sulfide, and then distilled under reduced pressure to collect the fraction at 90-100°C / -0.09MPa to obtain 1- (4'-Chlorophenyl)-2-methyl-1,2-propylene oxide, 657 g of fractions were collected.

[0051] Prod...

Embodiment 2

[0053] a) In a 2000ml flask, dissolve 365g (2mol) of 1-(4'-chlorophenyl)-2-methyl-1,2-propylene oxide in 200ml methanol, add 522g (5mol) morpholine, 20g Catalyst, heated to 80°C and refluxed for 8 hours, sampled and analyzed, GC detected that 1-(4'-chlorophenyl)-2-methyl-1,2-propylene oxide disappeared, first distilled methanol at normal pressure, and then started Distill under reduced pressure, recover the remaining methanol and excess morpholine, cool the concentrate to 50°C, add 200ml of toluene and stir to dissolve, filter out the catalyst, then add 360g of hydrochloric acid aqueous solution with a concentration of 20% by mass, and adjust the pH to 7. Leave to stand for stratification, transfer the water layer to another flask to participate in the next reaction, and recycle the toluene in the upper organic layer.

[0054] The preparation method of the catalyst is as follows: Weigh 1g of phosphotungstic acid (PW), 100g of Y-type molecular sieve and 10g of activated alumina...

Embodiment 3

[0060] a) In a 2000ml flask, 1-(4'-chlorophenyl)-2-methyl-1,2-propylene oxide 365g (2mol) was dissolved in 200ml methanol, and 565g (6.5mol) morpholine was added, 20g catalyst, heated up to 80°C and refluxed for 8 hours, sampled and analyzed, GC detected that 1-(4'-chlorophenyl)-2-methyl-1,2-epoxypropane disappeared, first distilled methanol at normal pressure, and then Start vacuum distillation, reclaim the remaining methanol and excess morpholine, cool to 50°C, add 200ml of toluene and stir to dissolve, filter out the catalyst, then add 360g of hydrochloric acid aqueous solution with a mass percentage concentration of 20%, adjust the pH=7, statically Set the layers, transfer the water layer to another flask to participate in the next reaction, and recycle the toluene in the upper organic layer.

[0061] The preparation method of the catalyst is as follows: Weigh 1g of phosphotungstic acid (PW), 100g of Y-type molecular sieve and 25g of activated alumina respectively, mix the...

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Abstract

The invention discloses a synthetic method of 2-methyl-1-(4'-methylthiophenyl)-2-morpholinyl-1-acetone, which comprises the following steps: carrying out ring-opening reaction on 1-(4'-chlorphenyl)-2-methyl-1, 2-propylene epoxide and morpholine and acidifying with hydrochloric acid to prepare 1-(4'-chlorphenyl)-2-methyl-2-morpholinyl-1-propyl alcohol hydrochloride; carrying out oxidizing reaction with oxygen and alkalifying to remove the hydrochloride, thereby preparing 1-(4'-chlorphenyl)-2-methyl-2-morpholinyl-1-acetone; and carrying out substitution reaction with sodium thiomethoxide to prepare the 2-methyl-1-(4'-methylthiophenyl)-2-morpholinyl-1-acetone. The method has the advantages of simple process, convenience in use, higher yield, less three-waste emission, low production cost and high raw material utilization rate, thereby having wide application prospect.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for synthesizing 2-methyl-1-(4'-methylthiophenyl)-2-morpholino-1-propanone. Background technique [0002] 2-Methyl-1-(4'-methylthiophenyl)-2-morpholino-1-propanone is a relatively new class of highly active photoinitiators with high photoinitiator efficiency. The structural formula is as follows : [0003] [0004] U.S. Patent No. 4582862A discloses a photocurable colored composition, which uses thioanisole and isobutyryl chloroform to react, and obtains the product 2-methyl-1-(4'- Methylthiophenyl)-2-morpholino-1-propanone; the synthetic route is as follows: [0005] [0006] The Fuckers reaction of the synthesis method will produce a large amount of aluminum trichloride wastewater and hydrochloric acid gas, and the bromination reaction atom utilization rate is very low, the reaction yield is low, and there is no competitive advantage in the market. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/104
Inventor 卢小逸鲁海华吴文良张启明董道敏邵琦王诚
Owner ZHEJIANG QIMING PHARMA
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