Synthesis method of o-tert-butyl aniline

A technology of o-tert-butylaniline and synthesis method, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve the problems of low reaction yield, cumbersome post-processing, high energy consumption, and achieve selectivity Good, good product quality, good yield effect

Pending Publication Date: 2022-07-22
安徽皓元药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] US4892974A discloses that aniline and isobutylene are prepared in a fixed-bed catalytic reactor at high temperature and high pressure using a silica-alumina catalyst to prepare o-tert-butylaniline, but there are N-tert-butylaniline, di-tert-butylaniline and benzene rings Impurities replaced by different positions
[0008] At present, the method reported in the prior art has many problems such as high energy consumption, tedious post-processing, and low reaction yield; , a synthetic method for o-tert-butylaniline suitable for large-scale production

Method used

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  • Synthesis method of o-tert-butyl aniline
  • Synthesis method of o-tert-butyl aniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1 Preparation of 2-(2-tert-butyl)phenoxy)acetic acid

[0061] 50.0 g of 2-tert-butylphenol and 500 mL of acetonitrile were added to a three-necked flask, 66.6 g of sodium hydroxide was added, the temperature was raised to 50° C., and stirring was started. 91.6g of 2-bromoacetic acid was added dropwise, the internal temperature was controlled to be 50±5°C, and the mixture was kept stirring for 4h. The reaction was monitored by TLC (petroleum ether:ethyl acetate=4:1) and the reaction was complete. Concentrate at 50 °C until no obvious droplets remain, add 500 mL of water and 350 mL of methyl tert-butyl ether, add 3N dilute hydrochloric acid to adjust pH=1~3, and use 350 mL of methyl tert-butyl ether for the aqueous phase after separation. Extracted, combined the organic phases and concentrated to dryness to obtain a light yellow solid, which was dried at 45°C to obtain 62.0 g, yield: 89.5%, see 1H NMR chart figure 1 shown.

Embodiment 2

[0062] Example 2 Preparation of 2-(2-tert-butyl)phenoxy)acetic acid

[0063] 25.0 g of 2-tert-butylphenol and 200 mL of methyl ethyl ketone were added to a three-necked flask, 33.3 g of sodium hydroxide was added, the temperature was raised to 55° C., and stirring was started. 45.8g of 2-bromoacetic acid was added dropwise, the internal temperature was controlled to be 50±5°C, and the mixture was kept stirring for 4h. The reaction was monitored by TLC (petroleum ether:ethyl acetate=4:1) and the reaction was complete. Concentrate at 50°C until no obvious droplets remain, add 250 mL of water and 170 mL of methyl tert-butyl ether, add 3N dilute hydrochloric acid to adjust pH=1~3, and use 150 mL of methyl tert-butyl ether for the aqueous phase after separation. Extracted, combined the organic phases and concentrated to dryness to obtain a light yellow solid, which was dried at 45°C to obtain 32.5 g, yield: 93.7%.

Embodiment 3

[0064] Example 3 Preparation of 2-(2-tert-butyl)phenoxy)acetic acid

[0065] 45.0 g of 2-tert-butylphenol and 500 mL of toluene were added to a three-necked flask, 66.6 g of sodium hydroxide was added, the temperature was raised to 70° C., and stirring was started. Add 82.5 g of 2-bromoacetic acid dropwise, control the internal temperature to be 50±5°C, and keep stirring for 5h. The reaction was monitored by TLC (petroleum ether:ethyl acetate=4:1) and the reaction was complete. 500 mL of water was added, and 3N dilute hydrochloric acid was added to adjust pH=1~3. After liquid separation, the organic phase was concentrated to dryness to obtain a pale yellow solid, which was dried at 45° C. to obtain 50.3 g, yield: 80.6%.

[0066]

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Abstract

The invention discloses a synthesis method of o-tert-butyl aniline. The reaction formula is shown in the specification, wherein R1 and R2 are independently selected from CH3 or H; the preparation method comprises the following steps: carrying out a heating reaction on a compound shown in a formula III and alkali in an organic solvent to obtain an o-tert-butyl aniline compound, wherein the molar ratio of the compound shown in the formula III to the alkali is 1: (3.5-7.5). The synthesis method provided by the invention overcomes the problem of low yield of aryloxy amide of which the ortho-position is a tert-butyl electron-donating group in the prior art, the yield reaches 70% or above, and the synthesis method is high in safety, low in cost, good in selectivity, high in yield and suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a method for synthesizing o-tert-butylaniline. Background technique [0002] o-tert-Butylaniline is an important fine chemical product, widely used in medicine, pesticides, dyes, polymer chemicals and other fields. [0003] CN114085180A, CN114057627A and WO2021250648A1 disclose that o-tert-butylaniline can be used as a catalyst ligand for the synthesis of (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2 - Methyl carboxylate, this fragment is a key intermediate compound in the synthesis of the new crown drug nematevir tablets. [0004] CN112023979A discloses a method for synthesizing o-tert-butylaniline by alkylation of aniline and methyl tert-butyl ether under the action of phosphotungstic acid (DTP) / HZSM-5 catalyst in an autoclave. The method can make In the reaction product of aniline and methyl tert-butyl ether, the selectivity of o-tert-butyl aniline is greatly improve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/45
CPCC07C209/00C07C51/367C07C231/02C07C211/45C07C59/125C07C235/06
Inventor 杨绍波金飞敏朱晓峰王子坤张国平刘超高强郑保富
Owner 安徽皓元药业有限公司
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