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4-biphenyl methanol synthetic method

A biphenylmethanol and synthesis method technology, applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve the problems of high production raw material cost, unsuitable for scale-up production, etc., and achieve low price and easy operation , The effect of easy access to raw materials

Active Publication Date: 2015-12-30
浦拉司科技(上海)有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] However, in the second synthetic method, 4-chlorobenzyl alcohol, phenylboronic acid, and expensive palladium catalysts are used, and the cost of raw materials is too high, so it is not suitable for scale-up production

Method used

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  • 4-biphenyl methanol synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Into a 3L autoclave, add biphenyl (350g, 2.27mol), cuprous chloride (1.0g, 0.01mol), paraformaldehyde (90g, 1.0mol), 85% phosphoric acid (270g) and concentrated hydrochloric acid (1050g) ), the reaction system is closed, the pressure in the kettle is about 3 atmospheres, slowly heated and stirred to 120°C, reacted for 36 hours, HPLC detects the reaction, cools down, down to 30°C, stands still, removes the lower water layer, and adds to the reaction kettle Water (1400g), start stirring, heat up, heat to 100°C and reflux, react for 24 hours, then cool down to room temperature, filter to obtain a crude product, recrystallize with three times the amount of toluene to obtain 217 grams of white solid, and pass the conventional The structure confirmation method was confirmed to be 4-biphenylmethanol, the purity detected by HPLC: 98%, and the yield: 52%.

[0052] Nuclear magnetic confirmation of the structure of the white solid (final product) 1 HNMR: (400MHz, CDCl3) δ: 4.73 (s, 2...

Embodiment 2

[0054] Add biphenyl (350g, 2.27mol), cuprous chloride (1.0g, 0.01mol), paraformaldehyde (90g, 1.0mol), 85% phosphoric acid (270g) and concentrated hydrochloric acid (1050g) to a 3L three-necked flask. ), a conventional normal pressure reaction system, slowly heat and stir to 120°C, react for 36 hours, HPLC check the reaction, cool down, drop to 30°C, stand still, remove the lower water layer, add water (1400g) to the reactor, and start stirring Raise the temperature, heat to 100°C and reflux, react for 24 hours, then cool down to room temperature, filter to obtain the crude product, recrystallize with three times the amount of toluene to obtain 129 grams of white solid, and by conventional structure confirmation methods, the confirmation is 4 -Biphenylmethanol, purity detected by HPLC: 98%, yield: 31%.

[0055] Nuclear magnetic confirmation of the structure of the white solid (final product) 1 HNMR: (400MHz, CDCl3) δ: 4.73 (s, 2H), 7.35 (m, 1H), 7.44 (m, 4H), 7.59 (d, 4H, J=8.0)....

Embodiment 3

[0057] Into a 3L three-neck flask, add biphenyl (350g, 2.27mol), paraformaldehyde (90g, 1.0mol), 85% phosphoric acid (270g) and concentrated hydrochloric acid (1050g), normal pressure reaction system, slowly heating and stirring to 120°C, react for 36 hours, HPLC detects the reaction, cools down, drops to 30°C, stands still, removes the lower water layer, adds water (1400g) to the reaction kettle, starts to stir and raises, heat to 100°C to reflux, and react for 24 hours. Then, it was cooled to room temperature and filtered to obtain a crude product, which was recrystallized with three times the amount of toluene to obtain 90 g of a white solid, which was confirmed to be 4-biphenylmethanol by conventional structure confirmation methods. Its purity as determined by HPLC: 98 %, yield: 22%.

[0058] Nuclear magnetic confirmation of the structure of the white solid (final product) 1 HNMR: (400MHz, CDCl3) δ: 4.73 (s, 2H), 7.35 (m, 1H), 7.44 (m, 4H), 7.59 (d, 4H, J=8.0).

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Abstract

The invention discloses a 4-biphenyl methanol synthetic method. The method comprises the steps that 1, biphenyl, paraformaldehyde, phosphoric acid, concentrated hydrochloric acid and a catalyst are mixed and heated to 100-120 DEG C, and are subjected to a reaction in a closed system for 2-48 h, cooled and layered into a water layer and an organic layer; 2, the water layer obtained in the step 1 is removed, water is added into the organic layer, heating reflux is performed for 8-48 h, cooling and filtering are performed, and a crude product is obtained; 3, an organic solvent is used for achieving recrystallization on the crude product obtained in the step 2, and 4-biphenyl methanol is obtained. The 4-biphenyl methanol synthetic method has the advantages of being capable of obtaining raw materials easily, low in cost, suitable for industrial production and the like.

Description

Technical field [0001] The invention relates to a method for synthesizing a compound, in particular to a method for synthesizing 4-biphenylmethanol. Background technique [0002] 4-Biphenylmethanol is an important intermediate for a new material and also an important raw material for the synthesis of pharmaceutical intermediates. [0003] At present, the synthesis methods of 4-biphenylmethanol reported in the literature mainly include the following two: [0004] 1) The first synthesis method [0005] Using 4-bibenzoic acid as a raw material, it is firstly catalyzed with methanol or glycolic acid to form an ester, and then subjected to sodium borohydride reduction or high-pressure catalytic hydrogenation reaction to obtain the target compound. The synthesis route is as follows: [0006] [0007] Among them, the specific steps of the first synthesis method are as follows: [0008] A). Stir and mix 4-bibenzoic acid with methanol / ethanol, then add a small amount of concentrated sulfuric aci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/24C07C29/124
Inventor 漆伟君蔡伟兵陆电云
Owner 浦拉司科技(上海)有限责任公司
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