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Method for preparing o-amino-p-tertiary butyl phenol

A technology of p-tert-butylphenol and o-amino, which is applied in the field of synthesis of organic compounds, can solve the problems of serious pollution, cumbersome operation, and high cost, and achieve the effects of high reaction yield, easy operation, and small investment in equipment

Inactive Publication Date: 2010-04-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method is cumbersome to operate, the route is long, the cost is high, and the pollution is still serious due to the diazo coupling process

Method used

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  • Method for preparing o-amino-p-tertiary butyl phenol
  • Method for preparing o-amino-p-tertiary butyl phenol
  • Method for preparing o-amino-p-tertiary butyl phenol

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Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1, a kind of preparation method of o-amino p-tert-butylphenol, take o-nitro-p-tert-butylphenol as starting raw material, carry out the following steps successively:

[0024] (1) 39.0g (0.2mol) of o-nitro-p-tert-butylphenol, 200mL of 95% ethanol aqueous solution, 2.5g of FeCl 3 ·6H 2 0, 12g gacs are dropped into 500mL there-necked flask together, be warmed up to reflux 15min, then slowly dropwise (20 drops / min) 40g hydrazine hydrate solution (N 2 h 4 ·H 2 The mass percent content of O is 50%, 0.4mol), after the dropwise addition is completed, 2 g of hydrosulfite (sodium dithionite) is added, and the reflux is continued for 3 h.

[0025] (2) After the reaction is completed, filter slightly cold, transfer the filtrate to a 500mL eggplant-shaped flask, add 100mL of water, and distill under reduced pressure to remove ethanol; there is product precipitation, cooling, and filtration; the precipitated product is washed with water and dried to obtain a white flake ...

Embodiment 2

[0027] Embodiment 2, a kind of preparation method of o-amino-p-tert-butylphenol, using o-nitro-p-tert-butylphenol as starting raw material, carries out the following steps successively:

[0028] (1) 39.0g (0.2mol) o-nitro-p-tert-butylphenol, 200mL methanol, 5.0gFeCl 3 ·6H 2 0, 12g gacs are dropped into 500mL there-necked flask together, be warmed up to reflux 15min, then slowly drip 28.6g hydrazine hydrate solution (N 2 h 4 ·H 2 The mass percent content of O is 70%, 0.4 mol), after the dropwise addition, 0.39 g of hydrosulfite (sodium dithionite) is added, and the reflux is continued for 4 hours.

[0029] (2) After the reaction is completed, filter it slightly cold, transfer the filtrate to a 500mL eggplant-shaped flask, add 100mL of water, distill under reduced pressure to remove methanol, and a product precipitates, cools, and filters; the precipitated product is washed with water and dried to obtain a white flake Crystal 32.5g, yield 97.3%, melting point 161-162°C.

[...

Embodiment 3

[0031] Embodiment 3, a preparation method of o-amino-p-tert-butylphenol, using o-nitro-p-tert-butylphenol as a starting material, the following steps are carried out in sequence:

[0032] (1) 39.0g (0.2mol) of o-nitro-p-tert-butylphenol, 200mL of 99% methanol aqueous solution, 1.5g of FeCl 3 ·6H 2 0, 12g gacs are dropped into 500mL there-necked flask together, be warmed up to reflux 15min, then slowly drip 22.2g hydrazine hydrate solution (N 2 h 4 ·H 2 The mass percent content of O is 90%, 0.4 mol), after the dropwise addition is completed, 0.8 g of hydrosulfite (sodium dithionite) is added, and the reflux is continued for 4 hours.

[0033] (2) After the reaction is completed, filter it slightly cold, transfer the filtrate to a 500mL eggplant-shaped flask, add 100mL of water, distill under reduced pressure to remove methanol, and a product precipitates, cools, and filters; the precipitated product is washed with water and dried to obtain a white flake The crystal is 30.9g,...

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Abstract

The invention discloses a method for preparing o-amino-p-tertiary butyl phenol. The o-amino-p-tertiary butyl phenol is prepared through reducing reaction by using the o-nitro-p-tertiary butyl phenol as a raw material and hydrazine hydrate as a hydrogen source under the action of a catalyst, wherein the catalyst is FeCl3, salts containing crystal water of the FeCl3 or aqueous solution of the FeCl3; the molar ratio of the FeCl3 and the o-nitro-p-tertiary butyl phenol is between 1 percent and 10 percent; and the molar ratio of the hydrazine hydrate and the o-nitro-p-tertiary butyl phenol is 1.6-2.5:1. The method has the characteristics of succinct process, high yield, low cost, less discharge of the three wastes, and the like.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing o-amino-p-tert-butylphenol (2-amino-4-(tert-butyl)phenol). Background technique [0002] o-amino-p-tert-butylphenol, which has the molecular formula C 10 h 15 NO, its structural formula is shown in S-1, the pure product is white to off-white crystalline powder, melting point 164-166 °C, soluble in ethanol, ether and chloroform, hardly soluble in benzene, almost insoluble in cold water, is an important fine Chemical intermediates, mainly used in the synthesis of fluorescent whitening agents OB, MN, EFT, ER, ERM and other products. [0003] [0004] According to comprehensive literature reports, the preparation of o-amino p-tert-butylphenol adopts the following methods at present: [0005] Method 1. Use p-tert-butylphenol, and then use catalytic hydrogenation or alkali sulfide reduction to prepare o-amino-p-tert-butylphenol after nitrati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/76C07C213/02
Inventor 陈新志计立钱超
Owner ZHEJIANG UNIV
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