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Method for preparing 4,4'-dihydroxy benzophenone

A technology of dihydroxybenzophenone and phenyl hydroxybenzoate, which is applied in 4 fields, can solve the problems of limited catalyst types, serious environmental pollution, and difficult recovery of waste phosphoric acid, etc., to reduce production costs, simplify processes, and achieve high yields Effect

Inactive Publication Date: 2006-08-30
WUHAN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

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

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-necked flask. After stirring, add a catalytic amount of concentrated sulfuric acid. Heat at 65°C to react for 2h. Discharge the material and pour it into ice water. Stir to separate the solid and filter. Recrystallize from ethanol to obtain a white solid. P-acetoxybenzoic acid, the yield is 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) in a three-necked flask equipped with a stirring and reflux condenser, and raise the temperature to 70~75℃ The reaction was stirred for 3h until no gas escaped. After cooling to room temperature, the unreacted thionyl chloride was distilled off, and the residue was distilled under reduced pressure to collect the 140-144°C / 10.67kPa fraction to obtain 29 g (0.15 mol) of light yellow oily liquid p-acetoxybenzoyl chloride.

[...

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] Chlorobenzene was used as the solvent, and the reaction was refluxed 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 the solvent, and the reaction is heated and stirred at reflux 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. The yield was 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] Chlorobenzene was used as the solvent, and the reaction was refluxed for 10 hours to prepare phenyl p-acetoxybenzoate with a yield of 96%.

[0033] Phenyl p-hydroxybenzoate: chromium trifluoromethanesulfonate is 1:0.15 (molar ratio), cyclohexane is the solvent, and the reaction is heated and stirred at 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. The yield was 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 chemicals and relates to a preparation method of 4,4'-dihydroxybenzophenone. Background technique [0002] 4,4'-Dihydroxybenzophenone is a chemical and pharmaceutical intermediate. Its structural formula is: [0003] [0004] There are many reports on its synthesis. Among them, Japanese patent JP 3123752 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. This method is also used in the industry to synthesize. The type of catalyst used in the method is limited, waste phosphoric acid is difficult to recycle, causing serious environmental pollution and high cost. Summary of the invention [0005] The purpose of the present invention is to overcome the deficiencies in the prior art and provide a new synthetic route and method for 4,4'-dihydroxybenzophenone. The method has ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/83C07C45/54
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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