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Preparation method of 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid

A technology of o-hydroxyphenyl and cyclopropane, which is applied in the field of preparation of 2-cyclopropane-1-carboxylic acid, can solve the problems of expensive reagent TMSOI, difficulty in large-scale preparation, and poor reaction yield, and achieve low cost of raw materials and reagents , easy to large-scale industrial production, ideal yield effect

Active Publication Date: 2014-12-17
SHANGHAI AIPU VEGETABLE TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The main problems of these reported technical solutions are that the reagent TMSOI is expensive, the reaction yield is poor, and there are many raw materials mixed in the product, which leads to complicated post-treatment and is difficult to prepare on a large scale.

Method used

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  • Preparation method of 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid
  • Preparation method of 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthetic route of the 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid of the present embodiment is as follows:

[0032]

[0033] (A) Synthesis of o-methoxystyrene (compound 2)

[0034] In a dry 100mL single-necked bottle, add o-methoxycinnamic acid (compound 1, 25g, 0.14mol), potassium hydroxide (17g, 0.3mol) and 60mL of ethylene glycol in sequence. The mixture was heated to reflux for 1 hour, followed by distillation to collect fractions at 140-150°C. When the temperature rose to 180°C, the distillation was stopped. 15.6 g of a light yellow oil was obtained, namely o-methoxystyrene (compound 2), with a yield of 83%. The GC purity is 95%, and it can be directly used in subsequent reactions without purification. (B) Synthesis of 1-o-methoxyphenyl-1,2-dibromoethane (compound 3)

[0035] In a 150 mL round bottom flask, compound 2 (13.4 g, 0.1 mol) and 100 mL of chloroform were added. Under stirring, slowly add 50 mL of chloroform solution containing bromine (...

Embodiment 2

[0044] The same as Example 1, the difference is that this example investigated the reaction temperature, reaction time, reaction solvent, and different bases in the step (A) of Example 1. The influence of different bases on the reaction to generate compound 2 (ie conversion rate), the results are shown in the table 1 shows:

[0045] The impact of different reaction conditions on the yield of compound 2 in table 1

[0046]

Embodiment 3

[0048] Same as Example 1, the difference is that this example examines different reaction temperatures, reaction times, and reaction solvents in Step (B) of Example 1, compound 2: Br 2 The effect of the molar ratio on the reaction to generate compound 3 (i.e. conversion rate), the results are shown in Table 2:

[0049] The impact of different reaction conditions on the yield of compound 3 in table 2

[0050]

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Abstract

A preparation method of 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid is provided. With o-alkoxy cinnamic acid as a raw material, 2-(o-alkoxyphenyl)cyclopropane-1,1-ethyl dicarboxylate is obtained through pyrolysis decarboxylation, halogen addition and cyclopropanation, and then the novel tobacco spice 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid is prepared through deestering, hydrolysis, demethylation and other steps. The raw material and reagents in the route are all commercial products, so that the raw material is easy to obtain; the reaction steps are all classic organic reactions, especially the cyclopropanation step avoids the use of expensive trimethylsulfoxonium halogen (TMSOX, wherein X is Cl, Br or I) reagents, and thus the cost of production is significantly reduced. Through process optimization, the overall yield of the reaction reaches 53%. The method has the advantages of simple operation, high synthesis yield, low costs of the raw material and the reagents, easy scale production and the like. The 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid prepared by the method is mainly used in spice and essence industries.

Description

technical field [0001] The present invention belongs to the synthesis method of spices, in particular, relates to a method for preparing 2-(o-hydroxyphenyl)cyclopropane-1-carboxylic acid. Background technique [0002] Coumarin, aroma and taste are one of the important quality characteristics of tobacco products. Many spices can enhance and improve the aroma and taste of tobacco products to varying degrees. Among these spices, coumarin derivatives are commonly used substances that can increase the natural flavor of tobacco itself, and are widely used in the formulation of tobacco flavors and the flavoring of tobacco products (Liu Shuwen, "Technical Handbook of Synthetic Flavors"). Better flavors for tobacco can be obtained by modifying the structure of coumarin compounds. For example: hydrolyzing coumarin, hydrogenated coumarin, cycloprocoumarin and epoxycoumarin under alkaline conditions, and acidifying to obtain a class of hydroxycarboxylic acids that can significantly en...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/757C07C62/06C07C51/377
CPCC07C41/18C07C41/22C07C51/09C07C51/377C07C51/38C07C67/343C07C2601/02C07C43/215C07C43/225C07C69/757C07C62/06
Inventor 陆欣宇王慧辰朱为宏
Owner SHANGHAI AIPU VEGETABLE TECH
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