Method for preparing 4,4'-dihydroxy benzophenone

A technology of dihydroxybenzophenone and phenyl hydroxybenzoate, applied in 4 fields, can solve the problems of limited catalyst type, serious environmental pollution, difficult recovery of waste phosphoric acid, etc., and achieves reduction of production cost, simplified process and high yield Effect

Inactive Publication Date: 2005-11-16
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The type of catalyst used in this method is limited, and waste phosphoric a...

Method used

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  • Method for preparing 4,4'-dihydroxy benzophenone
  • Method for preparing 4,4'-dihydroxy benzophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0016] (1) p-acetoxybenzoic acid

[0017] Add p-hydroxybenzoic acid and acetic anhydride into a 250ml three-neck flask, stir and add a catalytic amount of concentrated sulfuric acid, heat at 65°C for 2 hours, pour the material into ice water, stir, precipitate solids, filter, and recrystallize ethanol to obtain a white solid p-Acetoxybenzoic acid, yield 93%, mp192-194.

[0018] (2) p-Acetoxybenzoyl chloride

[0019] Add 28g (0.16mol) of p-acetoxybenzoic acid, 40ml (0.55mol) of thionyl chloride and pyridine (0.06-0.1ml) into a three-necked flask equipped with a stirring and reflux condenser, and heat up to 70-75°C The reaction was stirred for 3h until no gas evolved. After cooling to room temperature, unreacted thionyl chloride was distilled off, and the residue was distilled under reduced pressure to collect fractions at 140-144°C / 10.67kPa to obtain 29g (0.15mol) of light yellow oily liquid p-acetoxybenzoyl chloride.

[0020] (3) Phenyl p-acetoxybenzoate

[0021] Add 15g (...

Embodiment 2

[0027] The preparation methods of p-acetoxybenzoic acid, p-acetoxybenzoyl chloride, and phenyl p-hydroxybenzoate are the same as in Example 1.

[0028] Using chlorobenzene as the solvent instead, reflux reaction for 10 hours to prepare phenyl p-acetoxybenzoate with a yield of 96%.

[0029] The ratio of phenyl p-hydroxybenzoate:trifluoromethanesulfonic acid is 1:0.2 (molar ratio), petroleum ether is used as solvent, and the temperature is raised, stirred and refluxed for 10 hours. Wash with 10% sodium bicarbonate solution and water, and recrystallize from methanol-water (1:3, volume ratio) to obtain the target compound 4,4'-p-dihydroxybenzophenone. Yield 98%. mp219~220℃.

Embodiment 3

[0031] The preparation methods of p-acetoxybenzoic acid, p-acetoxybenzoyl chloride, and phenyl p-hydroxybenzoate are the same as in Example 1.

[0032] Using chlorobenzene as the solvent instead, reflux reaction for 10 hours to prepare phenyl p-acetoxybenzoate with a yield of 96%.

[0033] Phenyl p-hydroxybenzoate: chromium trifluoromethanesulfonate at a ratio of 1:0.15 (molar ratio), cyclohexane as a solvent, and the temperature was raised to stir and reflux for 8 hours. Wash with 10% sodium bicarbonate solution and water, and recrystallize from methanol-water (1:3, volume ratio) to obtain the target compound 4,4'-p-dihydroxybenzophenone. Yield 99%. mp219~220℃.

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Abstract

A process for preparing the 4,4'-bihydroxybiphenyl methaneone includes mixing phenyl p-hydroxybenzoate with catalyst in organic solvent, heating while stirring, reaction, separating the resultant and recrystallizing.

Description

technical field [0001] The invention belongs to the field of fine organic chemical industry and relates to a preparation method of 4,4'-dihydroxybenzophenone. Background technique [0002] 4,4'-Dihydroxybenzophenone is a chemical and pharmaceutical intermediate, and its structural formula is: [0003] [0004] There are many reports on its synthesis, among which Japanese patent JP3123752 reports that p-hydroxybenzoic acid and phenol are used as raw materials, and polyphosphoric acid is directly used as a solvent for simultaneous catalysis to synthesize the target compound. At present, this method is also used in industry. The type of catalyst used in this method is limited, and waste phosphoric acid is difficult to recycle, causing serious environmental pollution and high cost. Contents of the invention [0005] The purpose of the present invention is to overcome the deficiencies in the prior art and provide a new 4,4'-dihydroxybenzophenone synthesis route and method....

Claims

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Application Information

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IPC IPC(8): C07C49/83
Inventor 束家有阮启蒙束怡陈颖朱墨刘起军全向阳
Owner WUHAN UNIV
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