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Preparing method of 3-alkoxy phenylcarbinol

A technology of alkoxybenzyl alcohol and bromophenyl alkyl ether, which is applied in the field of preparation of 3-alkoxybenzyl alcohol, can solve the problems of high raw material price, difficulty in obtaining, uneconomical, etc., and achieve high purity and mild reaction conditions , the effect of short operation time

Inactive Publication Date: 2015-11-25
JIANGXI RV PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Among the above-mentioned methods, the first two have the disadvantages that the price of raw materials is relatively high and they are not easy to obtain.
The third method needs to use extremely low temperature and has the disadvantage of some expensive reagents, which is not conducive to industrialization
The fourth method needs to use more reducing agent, which is less economical

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 3-methoxybenzyl alcohol:

[0029] Add 13.4g (0.55mol) of magnesium chips, 15g of tetrahydrofuran, and 1 grain of iodine into a 500mL four-necked bottle, add about 10g of a solution prepared by 93.5g (0.5mol) of m-bromoanisole, and 250g of tetrahydrofuran, and heat it to trigger. Observe that the color of iodine fades and bubbles are generated, the initiation is successful. After the initiation is successful, add the above solution dropwise, control the temperature at 60-65°C, keep the temperature at 60-65°C for about 2 hours after the addition is completed, and the reaction is complete by gas phase analysis;

[0030] Then add 16.5g (0.55mol in formaldehyde) of paraformaldehyde, control the temperature at 60-70°C, stir at this temperature for 1 hour after the addition, and the reaction is completed by gas phase analysis;

[0031] Pour the reaction solution into a 1000mL beaker, add 200mL of ice water, add 30% hydrochloric acid dropwise until the pH value i...

Embodiment 2

[0033] Preparation of 3-methoxybenzyl alcohol:

[0034] The amount of magnesium chips in Example 1 was changed to 14.6 g (0.6 mol), and the rest was the same as in Example 1. Finally, 51.5 g of 3-methoxybenzyl alcohol was obtained, with a content of 99.4% and a yield of 74.6%.

Embodiment 3

[0036] Preparation of 3-methoxybenzyl alcohol:

[0037] Add 13.4g (0.55mol) of magnesium chips, 15g of tetrahydrofuran, and 1 grain of iodine into a 500mL four-necked bottle, add about 10g of a solution prepared by 93.5g (0.5mol) of m-bromoanisole, 80g of tetrahydrofuran, and 220g of toluene, and heat Initiation, when the color of iodine fades and bubbles are observed, the initiation is successful. After the initiation is successful, add the above solution dropwise, control the temperature at 70-85°C, keep the temperature at 80-85°C for about 3 hours after the addition is completed, and conduct gas phase analysis. Complete response;

[0038] Then add 15g (0.50mol as formaldehyde) of paraformaldehyde, control the temperature at 60-75°C, stir at this temperature for 1 hour after the addition, and the reaction is completed by gas phase analysis;

[0039] Then pour the reaction solution into a 1000mL beaker, add 200mL ice water, add 30% hydrochloric acid dropwise until the pH val...

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PUM

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Abstract

The invention discloses a preparing method of 3-alkoxy phenylcarbinol, comprising the steps: (1) dissolving 3-bromobenzene alkyl ether into a solvent, thus generating a Grignard reagent (3-alkoxy) phenyl magnesium bromide with Mg under the action of an initiator; (2) adding paraformaldehyde into the Grignard reagent at 50-85 DEG C to generate a substitution product; (3) performing acid hydrolyzing on the substitution product to obtain 3-alkoxy phenylcarbinol. Raw materials adopted in the invention are lower in price, the preparing method is mild in reaction conditions, only post-treatment of one time is required after three steps of reaction, and operation time is short; the purity of the obtained 3-alkoxy phenylcarbinol is high and completely accords with the requirements on use as a medicine intermediate.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of 3-alkoxybenzyl alcohol. Background technique [0002] 3-Alkoxybenzyl alcohol is an important class of pharmaceutical intermediates, of which 3-methoxybenzyl alcohol is mainly used in the synthesis of sagrelate, which itself is a diuretic and can be used to treat glaucoma and mild cardiac edema Wait. [0003] At present, the main methods of synthesizing 3-methoxybenzyl alcohol are as follows: 1. Taking 3-methoxybenzaldehyde as raw material to obtain 3-methoxybenzyl alcohol through hydrogenation (Miyada, Takuma, etal.Organometallics, 33 (23), 6760-6770; 2014) or use a reducing agent such as sodium borohydride to obtain 3-methoxybenzyl alcohol (Zeynizadeh, Behzad, et al. Organic Chemistry: An Indian Journal, 9(12), 469-479; 2013). 2. Use 3-methoxy-4-hydroxybenzaldehyde to obtain 3-methoxybenzyl alcohol through dehydroxylation reductio...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C43/23C07F3/02
CPCC07C41/01C07F3/003C07F3/02
Inventor 徐步斌方贵
Owner JIANGXI RV PHARMA
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