Preparation method of 2,6-diethyl-4-methylphenol

A technology of methyl phenol and diethyl, which is applied in the field of preparation of 2,6-diethyl-4-methylphenol, can solve the problems of excessive three wastes, low yield, long route, etc., and achieve safe operation and high raw material The effect of easy availability and cheap raw materials

Active Publication Date: 2018-07-10
ZHEJIANG ZHUJI UNITED CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a long route, low yield, requires the use of a large amount of expensive metal catalysts, and has many wastes. The use of hydrogen has potential safety hazards and is not suitable for industrial production.

Method used

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  • Preparation method of 2,6-diethyl-4-methylphenol
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  • Preparation method of 2,6-diethyl-4-methylphenol

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Example 1: Preparation of 2,6-diethyl-4-methyl-2-cyclohexenone

[0021] Add 6.2g (0.115mol) of sodium methoxide into methanol, stir until the sodium methoxide dissolves, add 7.6g (0.048mol) of the raw material 2-ethyl-3-oxohexanoic acid methyl ester, raise the temperature to 60°C for reaction, and dropwise add formaldehyde 5.0 g (0.072 mol) of acrolein in methanol. After the reaction was complete, the temperature was lowered, ethyl acetate was added, washed with water, concentrated and purified to obtain 5.8 g of the product 2,6-diethyl-4-methyl-2-cyclohexenone with a yield of 72%. 1 H NMR (CDCl 3 ,500MHz,TMS):δ6.44-6.42(m,1H,),2.58-2.53(m,1H,),2.22-2.12(m,2H),2.10-2.05(m,1H),1.14-1.12( m,3H), 1.01-0.91(m,10H). 13 C NMR (CDCl 3 ,125MHz): δ201.46, 148.82, 139.94, 47.81, 35.86, 31.83, 22.386, 22.08, 21.55, 13.51, 12.79.

Embodiment 2

[0022] Example 2: Preparation of 2,6-diethyl-4-methyl-2-cyclohexenone and 2,6-diethyl-4-methyl-3-cyclohexenone

[0023] Add 4.6g (0.115mol) of sodium hydroxide into tetrahydrofuran, add 8.3g (0.048mol) of ethyl 2-ethyl-3-oxohexanoate as raw material, raise the temperature to reflux, and add 5.0g (0.072mol) of methacrolein dropwise. mol) solution in tetrahydrofuran. After the reaction is complete, lower the temperature, add ethyl acetate, wash with water, and concentrate to obtain 6.5g of 2,6-diethyl-4-methyl-2-cyclohexenone and 2,6-diethyl-4-methyl- The mixture of 3-cyclohexenone, the yield is 81%, and the ratio of the two as determined by GC-MS is 90:10.

Embodiment 3

[0024] Example 3: Preparation of 2,6-diethyl-4-methyl-2-cyclohexenone

[0025] Add 40.0g (1.00mol) of sodium hydroxide into THF / H 2 In the mixed solution of O, stir until the sodium hydroxide is dissolved, add 93.1 g (0.50 mol) of ethyl 2-ethyl-3-oxohexanoate as raw material, raise the temperature to reflux reaction, add dropwise 42.0 g (0.60 mol) of methacrolein mol) THF solution. After the reaction was complete, the temperature was lowered, ethyl acetate was added, washed with water, concentrated and purified to obtain 58.2 g of the product 2,6-diethyl-4-methyl-2-cyclohexenone with a yield of 70%.

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Abstract

The invention provides a preparation method of 2,6-diethyl-4-methylphenol. The method uses a synthetic strategy which is completely different from the prior art, and comprises the following steps: taking 2-ethyl-3-oxohexanoate as a raw material; carrying out condensation reaction on the raw material and 2-methylacrolein under the effect of alkali to obtain an intermediate 2,6-diethyl-4-methyl-2-cyclohexenone and / or 2,6-diethyl-4-methyl-3-cyclohexenone; and carrying out aromatization on the 2,6-diethyl-4-methyl-3-cyclohexenone under the effect of a catalyst to obtain the target product 2,6-diethyl-4-methylphenol. Compared with the prior art, the method has the advantages that the raw materials are cheap and are easily obtained, an expensive metal catalyst and the corresponding ligand thereof are not required, the method is safe to operate, the three wastes are less and the like. Industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of synthesis of organic multi-substituted aromatic phenols, and in particular relates to a preparation method of 2,6-diethyl-4-methylphenol. Background technique [0002] Organic polysubstituted aromatic phenols are an important class of organic compounds. For example, 2,6-diethyl-4-methylphenol is an intermediate in the synthesis of the highly effective herbicide pinoxaden (WO2004 / 050607, WO00 / 78881). [0003] Currently, there are three methods for synthesizing 2,6-diethyl-4-methylphenol. [0004] The first method starts from 2,6-diethyl-4-methylaniline (WO2004 / 050607). 2,6-Diethyl-4-methylaniline is hydrolyzed by diazotization to obtain 2,6-diethyl-4-methylphenol. The raw material 2,6-diethyl-4-methylaniline used in the method is difficult to prepare, and a large amount of three wastes are generated in the diazotization step, and there are safety hazards, which are not conducive to industrial production. [0005...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/07C07C39/06C07C45/48C07C49/603
CPCC07C37/07C07C45/48C07C49/603C07C39/06
Inventor 孙殷卫王忠元陈邦池
Owner ZHEJIANG ZHUJI UNITED CHEM
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