Method for preparing 4-substituted oxyphenol compound

Abstract

The invention belongs to the field of organic synthesis, and relates to a method for preparing a 4-substituted oxyphenol compound. The method comprising the following steps: condensing hydroquinone and a halogen compound in a polar aprotic solvent in a reducing agent and metal alkali system to obtain the 4-substituted oxyphenol compound; removing the solvent after the above reaction, adding a non-polar solvent, filtering, washing, and recovering the raw material hydroquinone; and washing the obtained filtrate through using water, extracting by using an alkaline solution, and adjusting the pH value of the obtained extract solution to obtain the 4-substituted oxyphenol compound. The method has the advantages of short route, simple operation, high selectivity, high yield, good atom economy, high product content, recovery convenience and recycling of the raw material, reduction of three wastes and the cost, and suitableness for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a method for preparing 4-substituted oxyphenol compounds. Background technique [0002] Patent documents DE2908937, US4246419, US4266063, US4302242, US4216007 and Australian Journal of Chemistry, 48 (8), 1503-9; 1995 reported the synthesis of hydroquinone and 2-chloro-5-trifluoromethylpyridine derivatives, However, the selectivity is poor, and the yield is only 45%. The literature US4555575 and Synthetic Communications, 23 (20), 2845-9; 1993 discloses that methoxyphenol is condensed with halides, and then deprotected under acidic catalysis to synthesize, and the literature involves the methyl of hydroquinone The three-step reaction of protection, ether formation reaction and demethylation protection has complicated process and low overall yield. Patent JP2006036739A discloses that methanol / toluene mixed liquid is used as solvent, and the selectivity of hydroquinone is controlled b...

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Problems solved by technology

[0002] Patent documents DE2908937, US4246419, US4266063, US4302242, US4216007 and Australian Journal of Chemistry, 48 (8), 1503-9; 1995 reported the synthesis of hydroquinone and 2-chloro-5-trifluoromethylpyridine derivatives, However, the selectivity is poor, and the yield is only 45%

The literature US4555575 and Synthetic Communications, 23 (20), 2845-9; 1993 discloses that methoxyphenol is condensed with halides, and then deprotected under acidic catalysis to synthesize, and the literature involves the methyl of hydroquinone Three-step reaction of protection, ether formation reaction and demethylation protection, the process is complicated and the total yield is low

Patent JP2006036739A discloses that methanol / toluene mixed liquid is used as solvent, and the selectivity of hydroquinone is controlled by dropwise adding aqueous sodium hydroxide solution to synthesize 4-(3,3-dichloroallyloxy)phenol. Long, the process is loaded down with trivial details, yield is only 74.2%

In the above-mentioned documents, it is reported that the selectivity of synthesizing 4-substituted oxyphenol is relatively poor, and the reaction yield is not high. The post-treatment all adopts the method of directly importing into water, without reclaiming hydroquinone, and then extracting, resulting in a large amount of waste water. Solvent and Difficult recovery of hydroquinone, cost surge

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