New technology of synthesizing 4-[2-(cyclo propyl methoxy] ethyl] phenol

A technology of cyclopropylmethoxy and tert-butoxybenzene, applied in the field of preparing 4-[2-ethyl]phenol, which can solve the problems of long route, low yield and high price

Inactive Publication Date: 2005-08-10
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are deficiencies in the above methods, the method 1 synthetic route is longer, and the total yield is not high; the method 2 route is also longer, and the cost is also very high; although the method 3 synthetic route is short, the price of starting material p-hydroxyphenethyl alcohol is high , and the y

Method used

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  • New technology of synthesizing 4-[2-(cyclo propyl methoxy] ethyl] phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Embodiment 1: add 128.0 grams (1 mole) p-chlorophenol, 200 milliliters of toluene and a few drops of methanesulfonic acid in four-necked bottle, pass into isobutylene at 35 ℃, keep certain ventilation rate, ventilate at constant temperature for 10 After 1 hour, the amount of isobutene was controlled at 1.30 moles, reacted at 45° C. for another 15 hours, and weighed. Add a small amount of water, heat to drive off excess isobutylene, weigh after liquid separation, add alkali to wash twice to remove unreacted phenol, and weigh after washing. Then washed with water for 3-4 times, evaporated the solvent to obtain 153.0 g of crude product, and rectified under reduced pressure to obtain 141.0 g of p-chlorophenyl tert-butyl ether. The yield was 76.4%, and the content was 99.5% (GC).

[0013] IR(KBr): 2980, 1890, 1590, 1480, 1390, 1360, 1240, 1080, 1155, 1055, 890, 850 1 H-NMR (CDCl 3 / TMS): δ1.34 (9H, s), 6.90 (2H, d), 7.20 (2H, d)

Embodiment 2

[0014] Embodiment 2: Add 128.0 grams (1 mole) p-chlorophenol, 200 milliliters of chlorobenzene and a few drops of dilute sulfuric acid in a four-necked bottle, feed isobutylene at 15 ° C, keep a certain ventilation rate, and ventilate at a constant temperature for 10 After 1 hour, the amount of isobutene was controlled at 1.30 mol, reacted at 25° C. for another 15 hours, and weighed. All the other operations are the same as in Example 1, the yield of p-chlorophenyl tert-butyl ether is 68.8%, and the content is 99.5% (GC).

Embodiment 3

[0015] Example 3: Add 128.0 grams (1 mole) of p-chlorophenol, 200 milliliters of dichloromethane and a few drops of dilute sulfuric acid in a four-necked bottle, feed isobutylene at 25° C., keep a certain rate of ventilation, and ventilate at a constant temperature After 10 hours, the amount of isobutylene was controlled at 1.30 mol, and the reaction was carried out at 30° C. for another 15 hours, and the mixture was weighed. All the other operations are the same as in Example 1, the yield of p-chlorophenyl tert-butyl ether is 69.5%, and the content is 99.2% (GC).

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Abstract

A process for preparing 4-[2-(cyclopropyl methoxy)ethyl) phenol from P-chlorophenol includes such steps as phenohydroxy protecting, Grignard reacting, etherifying and hydrolyzing for removing protection.

Description

technical field [0001] The present invention relates to a new method for preparing 4-[2-(cyclopropylmethoxy)ethyl]phenol, in particular, it belongs to the category of organic synthesis. Background technique [0002] Betaxolol hydrochloride is a cardioselective β-adrenergic receptor blocker with endogenous sympathomimetic effect and strong effect. The pharmacological effect of human oral administration is 4 times that of propranolol and 5 times that of atenolol. The selectivity to the receptor is higher than that of metoprolol, the oral absorption rate is higher than that of atenolol, and the first pass effect is lower than that of metoprolol, so the bioavailability is higher than both of them, reaching 90%, and its half-life is as long as 20 Hour. In addition to treating high blood pressure and angina pectoris, the drug can also be used in the treatment of glaucoma with its 0.5% eye drops, and is a very promising drug. [0003] 4-[2-(cyclopropylmethoxy) ethyl] phenol is an...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C41/26C07C43/178
Inventor 孙飘扬马永林谢新开苟少华
Owner NANJING UNIV
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