Method for preparing 2-methyl-1-[4-(t-butyl)phenyl]-1-acetone

A technology of tert-butylbenzene and phenyl, which is applied in the field of preparation of chemical intermediate 2-methyl-1-[4-phenyl]-1-propanone, can solve the problem of affecting product content, low product effective content, removal and other problems, to achieve the effect of high content, good industrial application value and high reaction yield

Inactive Publication Date: 2014-12-31
INSIGHT HIGH TECH JIANGSU CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] Experimental result shows, will prepare high yield, the 2-methyl-1-[4-(tert-butyl) phenyl]-1-acetone product of high content, has bigger difficulty, also can also be produced when product A large number of impurities are generated, and these impurities cannot be removed by simple post-treatment methods, which not only affect the yield of the main product, but also affect the content of the product
Through a large number of experiments, the inventors have found the reason for generating a large number of impurities, mainly because the reaction raw materials will undergo alkyl migration in the presence of aluminum trichloride and at a higher temperature, resulting in the generation of a series of impurities. Thereby cause the effective content of product to be on the low side, the yield of product reduces

Method used

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  • Method for preparing 2-methyl-1-[4-(t-butyl)phenyl]-1-acetone
  • Method for preparing 2-methyl-1-[4-(t-butyl)phenyl]-1-acetone
  • Method for preparing 2-methyl-1-[4-(t-butyl)phenyl]-1-acetone

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Experimental program
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Effect test

Embodiment 1

[0030] In a 1000ml reaction bottle, add 53.3g (0.5mol) of isobutyryl chloride, 73.3g (0.55mol) of anhydrous aluminum trichloride, 340g of 1,2-dichloroethane, stir and cool down, keep at -20~0℃ drop Add 67.1g (0.5mol) of tert-butylbenzene, add dropwise for 2 hours, after the dropwise addition of tert-butylbenzene-20~0℃, react for 10 hours, stop the reaction, add the material to 500g of 10% hydrochloric acid for hydrolysis, and separate to obtain organic phase, the organic phase was washed with water to neutrality and rectified under reduced pressure to obtain 92.6g of 2-methyl-1-[4-(tert-butyl)phenyl]-1-acetone with a purity of 98.5%. The yield was 90.6% %. 1 HNMR (CDCl 3 , 400MHz) Characterization: δ1.21 (d, 6H, CH 3 ), δ1.46 (s, 9H, CH 3 ), δ3.62 (m, 1H, CH), δ7.63 (d, 2H, aromatic-H), δ7.80 (d, 2H, aromatic-H).

Embodiment 2

[0032] In a 1000ml reaction bottle, add 53.3g (0.5mol) of isobutyryl chloride, 80.0g (0.60mol) of anhydrous aluminum trichloride, 420g of 1,2-dichloroethane, stir and cool down, and keep at -20~0℃ drop Add 67.1g (0.5mol) of tert-butylbenzene, dropwise for 2.5h, after the dropwise addition of tert-butylbenzene-20~0℃, react for 8h, stop the reaction, add the material to 500g of 10% hydrochloric acid for hydrolysis, and separate to obtain Organic phase, after the organic phase was washed with water to neutrality, precipitation and rectification under reduced pressure obtained 93.2g of 2-methyl-1-[4-(tert-butyl)phenyl]-1-acetone with a purity of 98.2%. 91.2%. 1 HNMR (CDCl 3 , 400MHz) Characterization: δ1.21 (d, 6H, CH 3 ), δ1.46 (s, 9H, CH 3 ), δ3.62 (m, 1H, CH), δ7.63 (d, 2H, aromatic-H), δ7.80 (d, 2H, aromatic-H).

Embodiment 3

[0034] In a 1000ml reaction bottle, add 53.3g (0.5mol) of isobutyryl chloride, 86.7g (0.65mol) of anhydrous aluminum trichloride, 500g of 1,2-dichloroethane, stir and cool down, and keep it at -20~0℃ Add 67.1 g (0.5 mol) of tert-butylbenzene, dropwise for 3 hours, after the dropwise addition of tert-butylbenzene-20~0°C, react for 6 hours, stop the reaction, add the material to 500 g of 10% hydrochloric acid for hydrolysis, and separate to obtain organic phase, the organic phase was washed to neutrality and then rectified under reduced pressure to obtain 95.5g of 2-methyl-1-[4-(tert-butyl)phenyl]-1-acetone with a purity of 97.9%. The yield was 93.5% %. 1 HNMR (CDCl 3 , 400MHz) Characterization: δ1.21 (d, 6H, CH 3 ), δ1.46 (s, 9H, CH 3 ), δ3.62 (m, 1H, CH), δ7.63 (d, 2H, aromatic-H), δ7.80 (d, 2H, aromatic-H).

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Abstract

The invention relates to a method for preparing highly pure 2-methyl-1-[4-(t-butyl)phenyl]-1-acetone. The method comprises the following steps: carrying out a Friedel-Crafts reaction on raw materials comprising t-butylbenzene and isobutyryl chloride, hydrolyzing, washing by water, desolventizing, and carrying out reduced pressure distillation to obtain a final product. The method has the advantages of reduction of the generation of impurities through later dropwise addition of t-butylbenzene, high yield, safe post-treatmetn operation, industrial application value, and high purity of the 2-methyl-1-[4-(t-butyl)phenyl]-1-acetone product.

Description

technical field [0001] The invention relates to a preparation method of a chemical intermediate 2-methyl-1-[4-(tert-butyl)phenyl]-1-propanone. Background technique [0002] 2-Methyl-1-[4-(tert-butyl)phenyl]-1-propanone (Formula II) is an important chemical intermediate, which can be used to prepare hydroxyketone photoinitiators through halogenation reaction and hydrolysis reaction 2 -Hydroxy-2-methyl-1-[4-(tert-butyl)phenyl]-1-propanone (Formula III). [0003] [0004] Synthesis of 2-methyl-1-[4-(tert-butyl)phenyl]-1-propanone (Formula II), Document (1) Chemical Communications (Cambridge, United Kingdom), 2012, 48(56), 7034 -7036, literature (2) Organic Letters, 2012, 14(12), 3044-3047 and literature (3) Journal of the American Chemical Society, 1986, 108(2), 245-247 are reported. [0005] Document (1) discloses two synthetic methods, 2-iodopropane reacts with 4-tert-butylbenzoic acid (formula IV) and 4-tert-butylbenzoic anhydride respectively, and the yields are as hig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/76C07C45/46
CPCC07C45/46C07C45/80C07C45/82C07C45/85C07C49/76
Inventor 吴国平秦辉袁忠华李冬梅胡圣祥陆黎明孙贤范明罗必奎
Owner INSIGHT HIGH TECH JIANGSU CO LTD
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