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Preparation method of trimethylphloroglucinol

A technology of trimethylphloroglucinol and anhydrous phloroglucinol, which is applied in the field of medicine, can solve the problems of high product yield, reagent toxicity, and low safety, and achieve less by-products, easy operation, and improved safety sexual effect

Inactive Publication Date: 2021-09-17
HAIKOU TIANXINGJIAN PHARMA RES CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The invention provides a preparation method of trimethylphloroglucinol, which is used to solve the technical problems of low safety in the production process of the existing preparation method of trimethylphloroglucinol, high toxicity of reagents used and low yield of finished products

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  • Preparation method of trimethylphloroglucinol
  • Preparation method of trimethylphloroglucinol

Examples

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Embodiment 1

[0033] The present embodiment provides a kind of preparation method of trimethylphloroglucinol, comprising the following steps:

[0034] (1) Take 200ml of methanol and add it to the reaction bottle, slowly drop 64g of concentrated sulfuric acid under stirring; take 20.2g of anhydrous phloroglucinol into the reactor, stir until dissolved, fill with nitrogen, and then heat to 80°C for 6h under reflux .

[0035] Cool to room temperature, add 200ml of 20% sodium chloride solution, extract with methyl tert-butyl ether (100ml+50ml+50ml), combine the extracts, and distill at 60°C to recover the solvent to obtain a concentrate.

[0036] (2) Take the concentrate of step (1), add 180ml of dimethyl sulfoxide to dissolve, fill with nitrogen, add 66.4g of potassium carbonate, and raise the temperature to 130°C. Weigh 57.8g of dimethyl carbonate, divide it into three additions, each interval is 0.5h, continue to react for 1h after the addition, and then carry out distillation to remove unr...

Embodiment 2

[0040] The present embodiment provides a kind of preparation method of trimethylphloroglucinol, comprising the following steps:

[0041] (1) Take 200ml of methanol and add it to the reaction bottle, slowly drop 72g of 98% sulfuric acid solution under stirring; take 20.2g of anhydrous phloroglucinol into the reactor, stir until dissolved, fill with nitrogen, and then heat to 90°C to reflux Reaction 4h.

[0042] Cool to room temperature, add 200ml of 20% sodium chloride solution, extract with methyl tert-butyl ether (100ml+50ml+50ml), combine the extracts, and distill at 60°C to recover the solvent to obtain a concentrate.

[0043](2) Take the concentrate of step (1), add 180ml of dimethyl sulfoxide to dissolve until clear, fill with nitrogen, add 44.3g of potassium carbonate, and raise the temperature to 120°C. Weigh 72.2g of dimethyl carbonate, divide it into three additions, with an interval of 0.5h each time, continue to react for 2h after the addition, and then carry out d...

Embodiment 3

[0047] The present embodiment provides a kind of preparation method of trimethylphloroglucinol, comprising the following steps:

[0048] (1) Take 12L of methanol and add it to the reactor, slowly drop 3.84kg of 98% sulfuric acid solution under stirring; take 1.21kg of anhydrous phloroglucinol into the reactor, stir until dissolved, fill with nitrogen, and then heat to 90°C Reflux reaction 4h.

[0049] Cool to room temperature, add 12L of 20% sodium chloride solution, extract with methyl tert-butyl ether (6L+3L+3L), combine the extracts, and distill at 60°C to recover the solvent to obtain a concentrate.

[0050] (2) Take the concentrate of step (1), add 10.8 L of dimethyl sulfoxide to dissolve until clear, fill with nitrogen, add 3.98 kg of potassium carbonate, and raise the temperature to 140 °C. Weigh 4.33 kg of dimethyl carbonate, divide it into three additions, with an interval of 0.5 hours between each addition, continue to react for 2 hours, then carry out distillation ...

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Abstract

The invention discloses a preparation method of trimethylphloroglucinol. According to the invention, phloroglucinol is taken as a raw material, and sulfuric acid is adopted to catalyze a first-step reaction, so operation is simpler and more convenient, reaction byproducts are reduced, and damage to production equipment is reduced; and a reaction product obtained in the first-step reaction and dimethyl carbonate are subjected to a second-step methylation reaction, and dimethyl carbonate is non-toxic and non-corrosive, so production safety is greatly improved, the method is green and environment-friendly, and the quality and yield of a final finished product are improved. The method solves the problem of low safety in the production process of existing trimethylphloroglucinol preparation methods, avoids the use of strong corrosive reagents such as hydrochloric acid, and adopts dimethyl carbonate to replace a highly toxic reagent, namely dimethyl sulfate.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a preparation method of trimethylphloroglucinol. Background technique [0002] Trimethylphloroglucinol, whose chemical name is 1,3,5-trimethoxybenzene, is an important intermediate in organic synthesis, widely used in the synthesis of pharmaceuticals, pesticides and fine chemical products, such as for blood vessels Synthesis of the expander buflomedil hydrochloride. At the same time, trimethylphloroglucinol itself is an effective antispasmodic drug, which can directly act on smooth muscle, and through a synergistic effect, the sphincter and urethral smooth muscle are more sensitive to phloroglucinol, thereby strengthening the antispasmodic and analgesic effect. [0003] At present, there are two main methods of synthesizing trimethylphloroglucinol reported in China: one is to prepare trimethylphloroglucinol by using hexachlorobenzene as a raw material through two-step reaction ...

Claims

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Application Information

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IPC IPC(8): C07C37/16C07C39/10
CPCC07C37/16C07C39/10Y02P20/584
Inventor 李庆明凌秀才陈恳肖茂锐吴豪
Owner HAIKOU TIANXINGJIAN PHARMA RES CO LTD
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