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Method of preparing p-cyanophenol like compound

A technology of p-cyanophenol and compounds, which is applied in the field of p-cyano-substituted phenol compounds, can solve the problems of many side reactions, increase the difficulty and cost of production, and pollute the environment, so as to reduce costs and expenses, and solve pollution and hazards , the effect of mild reaction conditions

Inactive Publication Date: 2003-09-17
SICHUAN KELUN PHARMA CO LTD +1
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Problems solved by technology

In these preparation methods, not only need to use highly toxic cyanide, which will seriously pollute the environment, increase the problems and costs of waste treatment, but also seriously affect the health of operators and bring unsafe risks to operators , while the method has many side reactions, low yield and difficult separation, which increases the difficulty and cost of production

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  • Method of preparing p-cyanophenol like compound

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Embodiment 1

[0011] Embodiment 1: the preparation of 2-chloro-6-methyl p-cyanophenol

[0012] 154.5g (1.08mol) of 2-chloro-6-methylphenol was dissolved in 1000ml of trifluoroacetic acid, and 152g (1.08mol) of hexamethylenetetramine was added in batches at room temperature, and an exothermic reaction occurred. , then add 300ml trifluoroacetic acid to facilitate stirring. The float was heated to reflux overnight and the reaction mixture was cooled. Excessive trifluoroacetic acid was recovered by distillation under reduced pressure, and the mixture was poured into 3000ml of CH 2 Cl 2 , the organic layer was washed with water, and then each time with 500ml containing 10% K 2 CO 3 The solution was washed three times, the aqueous extract was acidified with concentrated hydrochloric acid, the precipitate was collected, and recrystallized with ethyl acetate to obtain 115 g of the corresponding p-hydroxybenzaldehyde compound (II), yield 62%, mp: 114-116°C.

[0013] Compound (II) was dissol...

Embodiment 2

[0015] Embodiment 2: the synthesis of 3.5-dimethyl p-hydroxybenzaldoxime

[0016] Add 15g (0.1mol) of 3,5-dimethyl p-hydroxybenzaldehyde (V), add NaOH solution (8g+50ml water), 7g of hydroxylamine hydrochloride, reflux the mixture for 4 hours, cool, and use 30% acetic acid under ice bath Adjust the pH to about 6, filter, wash with water, and recrystallize with chloroform to obtain 3,5-dimethyl-p-hydroxybenzaldehyde oxime (VI), 14.8g, yield 90.2%, mp: 83-85°C.

[0017] Put the obtained solid (VI) into the bottle, add 150ml of toluene, then add 0.5ml of concentrated sulfuric acid, stir and reflux and separate the water produced by the reaction, react for 2 hours, pour the saturated sodium phosphate solution into the reactant and mix, separate the water layer, concentrated a part, cooled and crystallized, and filtered to obtain 12 g of the target compound (VII) in light yellow needle-like crystals, 3,5-dimethyl-p-hydroxybenzonitrile, yield 90.9%, mp: 121-122C.

[0018] H-NMR...

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Abstract

A process for preparing p-cyanophenol compounds includes such steps as reaction between p-hydroxy benzaldehyde compound and hydroxyamine hydrochloride to obtain p-hydroxy benzaldehyde oxime, separating and dewatering reaction. Its advantage no need of highly toxic raw material, and gentle reaction condition.

Description

technical field [0001] The present invention relates to a new preparation method of p-cyano-substituted phenol compounds which can be used as important intermediates in fine chemical industry and pharmaceutical synthesis. Background technique [0002] Phenol derivatives substituted by p-cyano group are important intermediate compounds in fine chemical industry and pharmaceutical synthesis. For example, 4-hydroxy-3,5-dimethylbenzonitrile is an important intermediate compound in the synthesis of antiviral drug Pleconaril. The traditional synthesis and preparation methods of such compounds are all through the direct substitution reaction of highly toxic raw material cyanides such as sodium cyanide and cuprous cyanide. As mentioned in the synthesis of the intermediate compound in Drugs of the future1997.22 (1): 40~44, what just adopted is to be made of 4-bromo-2,6-dimethylphenol and Cu 2 CN 2 Obtained at reflux in DMF. In these preparation methods, not only need to use highl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/53
Inventor 张秋材丁敏李文忠程志鹏梁隆
Owner SICHUAN KELUN PHARMA CO LTD
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