Preparation method of 1,2-Dimethyl-3-methylsulfanyl-benzene

A technology of dimethyl anisole and nitro-o-xylene, applied in the field of preparation, can solve the problems of difficult "three wastes" treatment, high raw material prices, and high production costs, and achieves the advantages of being beneficial to industrialized production and the content of products. High and low cost effect

Active Publication Date: 2017-09-15
HUNAN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has a high yield and is easy to operate, but it is difficult to deal with the "three wastes" produced, the price of raw materials is high, the solvent has many side reactions in addition to participating in the main reaction, it is difficult to recycle, and the cost of industrialized comprehensive production is high.

Method used

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  • Preparation method of 1,2-Dimethyl-3-methylsulfanyl-benzene
  • Preparation method of 1,2-Dimethyl-3-methylsulfanyl-benzene
  • Preparation method of 1,2-Dimethyl-3-methylsulfanyl-benzene

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Embodiment 1

[0033] Under nitrogen protection, 61.1g (99%, 0.4mol) 3-nitro-o-xylene, 32.5g (95%, 0.44mol) sodium methyl mercaptide, 0.072g (98%, 0.0004mol) Nickel acetate, 1g (99%, 0.004mol) triphenylphosphine and 427.7g acetone were heated to 50°C and then kept for 20h. After the reaction, add water and toluene, separate the layers, dry the organic phase, and remove the solvent. The residue is rectified in a ceramic random packed tower, and 55.2 g of light yellow liquid 2,3-Di Tolyl sulfide, content 98.2%, yield 89%. 1 H NMR (CDCl 3 , 300MHz) δ: 2.29 (s, 6H, ArCH 3 ×2), 2.44(s, 3H, ArSCH 3 ), 6.97 (dd, J=6.9Hz, J=2.1Hz, 1H, C 6 h 3 -H), 7.03~7.12(m, 2H, C 6 h 2 ).GC-MS (m / z): 152.1 (M + ), 138, 105.1, 77, 45.

Embodiment 2

[0035] Under nitrogen protection, 61.1g (99%, 0.4mol) 3-nitro-o-xylene, 38.4g (95%, 0.52mol) sodium methyl mercaptide, 0.9g (98%, 0.004mol) Nickel bromide, 2.6g (99%, 0.008mol) tetrabutylammonium bromide and 244.4g N,N-dimethylformamide were heated to 70°C and then kept for reaction for 15 hours. After the reaction, add water and toluene, separate the layers, dry the organic phase, and remove the solvent. The residue is rectified in a ceramic random packed tower, and 53.1 g of light yellow liquid 2,3-bis Tolyl sulfide, content 98%, yield 85.5%.

Embodiment 3

[0037] Under nitrogen protection, 61.1g (99%, 0.4mol) 3-nitro-o-xylene, 59g (95%, 0.8mol) sodium methyl mercaptide, 2.6g (99%, 0.02mol) chlorine Nickel chloride, 0.16g (99%, 0.0004mol) methyl trioctyl ammonium chloride and 122.2g N,N-dimethylacetamide were heated to 80°C and then kept for 10h. After the reaction, add water and toluene, separate the layers, dry the organic phase, and remove the solvent. The residue is rectified in a ceramic random packed tower, and 53.4 g of light yellow liquid 2,3-bis Tolyl sulfide, content 98.5%, yield 86.4%.

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Abstract

The invention discloses a preparation method of 1,2-Dimethyl-3-methylsulfanyl-benzene. The preparation method comprises the following steps: under the protection of inert atmosphere, using 3-nitro-o-xylene as a raw material to be heated and reacted with sodium thiomethoxide in an organic solvent under action of nickel salt and a cocatalyst; and performing post-treatment on a reaction solution to obtain 1,2-Dimethyl-3-methylsulfanyl-benzene. The preparation method has advantages of high yield, low cost, simple operation, green and environmental protection and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a preparation method of 2,3-dimethylanisole sulfide. Background technique [0002] The English name of 2,3-dimethylanisole sulfide is 1,2-Dimethyl-3-methylsulfanyl-benzene, which is an important intermediate for the synthesis of the post-emergence herbicide oxentrazone, and is also used in the synthesis of other pesticides and medicines . Currently reported synthetic methods can be divided into 2,3-dimethylbromobenzene method and 2,3-dimethylaniline method according to raw materials. [0003] Akazome Motohiro et al [Journal of Organic Chemistry, 2010, 75 (3): 660-665] reported that 2,3-dimethylbromobenzene was prepared as Grignard reagent, and then reacted with dimethyl disulfide to obtain 2,3-disulfide Tolyl sulfide, yield 96%. The method has a high yield, but the raw materials are not easy to obtain, the reaction conditions are harsh, the react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C321/28
CPCC07C319/14C07C321/28
Inventor 罗先福刘国文高云英周锦萍王燕臧阳陵
Owner HUNAN CHEM RES INST
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