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Preparation method of 4-hydroxyphenethyl alcohol

A technology of p-hydroxyphenylethyl alcohol and p-bromophenol, which is applied in the field of preparation of p-hydroxyphenylethyl alcohol and can solve the problems of low yield and long fermentation time

Inactive Publication Date: 2014-05-21
徐州瑞赛科技实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many studies on its synthesis method. The early synthesis method is fermentation, the fermentation time is long, and the yield is low; p-Hydroxyphenylethanol, using lithium tetrahydrogen aluminum as a reducing agent, the yield per step can reach about 90%; there is also p-hydroxyphenylethanol prepared from phenylethylamine through digestion, reduction, diazotization, and hydrolysis. But the productive rate is very low, only about 45%; take phenylethyl alcohol as raw material, obtain p-hydroxyphenylethyl alcohol through esterification, nitration, reduction, hydrogenation, and the productive rate can reach about 70%.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Embodiment 1, the preparation of p-ene phenoxy bromobenzene:

[0012] Add 7g (0.04mol) of p-bromophenol, 5.1g (0.04mol) of 3-bromopropene and 30mL of acetone into a 100mL four-necked flask equipped with a mechanical stirrer, a star condenser and a thermometer, and add 5.4g (0.04mol) of acetone under vigorous stirring. mol) anhydrous potassium carbonate. Heat the water bath to 55°C and reflux for 4 hours, filter with suction, and distill at atmospheric pressure to obtain 14mL of acetone, then distill under reduced pressure (10kPa) to collect fractions at 158°C~162°C to obtain 6.4g of an oily colorless transparent liquid with a pungent odor. 74.3%.

Embodiment 2

[0013] Embodiment 2, the preparation of p-allyloxyphenethyl alcohol

[0014] Since the Grignard reaction has very strict requirements on the experiment, the reactants and experimental equipment should be properly treated before the experiment.

[0015] A. Preparation of anhydrous tetrahydrofuran (THF)

[0016] Step 1, check whether peroxide exists

[0017] Take THF 1~2mL, add an equal volume of 2% KI starch solution and a few drops of dilute hydrochloric acid, if it is purple or blue, it contains or oxide, and the second step is required, if it is colorless or slightly yellow, it means no Peroxide, step III can be carried out directly.

[0018] Step II, remove peroxide

[0019] Add 1.2 mL of concentrated sulfuric acid dropwise to 22 mL of water, then add 1.2 g of ferrous sulfate, and stir to dissolve. Put 100mL tetrahydrofuran in a 250mL separatory funnel first, add ferrous sulfate solution into it, plug the stopper and shake vigorously (deflate), separate layers, discard ...

Embodiment 3

[0030] Embodiment 3, the preparation of p-hydroxyphenethyl alcohol

[0031] Add 0.7g (0.018mol) of sodium borohydride, 2.5g (0.014mol) of p-phenoxyphenylethanol and 20mL of anhydrous tetrahydrofuran into a 100mL four-neck flask, cool down to -5°C with ice-salt mixture, and drop Add 1.8g (0.007mol) of iodine and 10mL of anhydrous tetrahydrofuran to form a solution. Control the rate of addition to keep the temperature between -2°C and 0°C, continue the reaction for 20 minutes after dropping for about 15 minutes, add 15 mL of methanol dropwise to terminate the reaction, distill at normal pressure, and filter to obtain a light yellow liquid (mixture).

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PUM

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Abstract

The invention relates to a preparation method of 4-hydroxyphenethyl alcohol. The preparation method is characterized in that: p-bromophenol is taken as a raw material, and is subjected to a series of reactions such as hydroxyl protection, Grignard reaction, and protecting group removing so as to obtain 4-hydroxyphenethyl alcohol. Product yield of the preparation method reaches about 90%.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular, the invention relates to a preparation method of p-hydroxyphenethyl alcohol. Background technique: [0002] Phenylethyl alcohol is an important pharmaceutical and spice intermediate, which can be used to synthesize a variety of useful drugs, such as: Metoprolol (Metoprolol), which is used for the treatment of hypertension, angina pectoris, arrhythmia and myocardial infarction, and can also be used for Hyperthyroidism, migraine; Betaxolol (Betaxolol), treatment of high blood pressure, open-angle glaucoma; Breast swelling and pain caused by weaning or milk stasis in rich women. [0003] There are many studies on its synthesis method. The early synthesis method is fermentation, the fermentation time is long, and the yield is low; p-Hydroxyphenylethanol, using lithium tetrahydrogen aluminum as a reducing agent, the yield per step can reach about 90%; there is also p-hydrox...

Claims

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Application Information

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IPC IPC(8): C07C39/11C07C37/055
CPCY02P20/55C07C37/055C07C41/16
Inventor 胡晓王理想王友志郭麦平胡丹红胡曼曼
Owner 徐州瑞赛科技实业有限公司
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