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Method of preparing heliotropin by using p-methyl phenol as raw material

A technology of p-cresol and jasmonal, which is applied in the direction of organic chemistry, can solve the problems of low total yield, low reaction yield, and easy agglomeration, and achieve low cost, ecological environment protection, and low price. Effect

Inactive Publication Date: 2006-06-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although with the development of basic raw materials such as catechol and glyoxylic acid, the cost of raw materials has decreased, but in the three-step reaction, the first two steps are not easy to control, and agglomeration is prone to occur; The rate is low, less than 50%, so the total yield is low

Method used

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  • Method of preparing heliotropin by using p-methyl phenol as raw material
  • Method of preparing heliotropin by using p-methyl phenol as raw material
  • Method of preparing heliotropin by using p-methyl phenol as raw material

Examples

Experimental program
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Effect test

Embodiment 1

[0037] P-cresol 108g (1mole), acetic anhydride 408g (4mole), 98% H 2 SO 4 0.5 g was added into a four-necked reaction flask equipped with a stirrer, a thermometer, and a reflux condenser, and the temperature was raised to react under reflux for 1 hour. Distillation gave 138 g (0.92 mole) of the target product with a yield of 92%.

[0038] The product 138g (0.92mole) that last step obtains and AlCl 3160g (1.2 mole) was mixed, added to a four-necked reaction flask equipped with a stirrer, thermometer, feeder, and reflux condenser, heated to 90°C for 2 hours, and then heated to 160°C for 2 hours. After the reaction was completed, the mixed solution was cooled to 90° C., and the pH value of the system was adjusted to 5.2 with acid. Add 200 ml of toluene to extract the reaction solution twice into the system, combine the toluene phases, and recover the toluene to obtain 126.4 g (0.837 mole) of the target product, with a yield of 91%.

[0039] The product 126.4g (0.837mole) that...

Embodiment 2

[0045] P-cresol 216g (2.0mole), acetic anhydride 816g (8mole), 98% H 2 SO 4 1 g was added into a four-necked reaction flask equipped with a stirrer, a thermometer, and a reflux condenser, and the temperature was raised to react under reflux for 1.5 hours. Unreacted acetic anhydride and acetic acid produced by the reaction may be by-products. Distillation gave 279.6 g (1.864 mole) of the target product with a yield of 93%.

[0046] The product 279.6g (1.864mole) that last step obtains and AlCl 3 320g (2.4 mole) were mixed, added to a four-necked reaction flask equipped with a stirrer, thermometer, feeder, and reflux condenser, heated to 100°C for 2 hours, and then heated to 165°C for 3 hours. After the reaction was completed, the mixed solution was cooled to 100°C, and the pH value of the system was adjusted to 5.6°C by adding dilute acid. In the system, 400ml of toluene was added twice to extract the reaction solution, the toluene phase was combined, and the toluene was re...

Embodiment 3

[0053] 486g (4.5mole) of p-cresol, 1836g (18mole) of acetic anhydride, 98% H 2 SO 4 2 g was added into a four-necked reaction flask equipped with a stirrer, a thermometer, and a reflux condenser, and the temperature was raised to react under reflux for 2 hours. Distillation gave 619.5 g (4.13 mole) of the target product, with a yield of 91.7%.

[0054] The product 619.5g (4.13mole) that last step obtains and AlCl 3 720g (5.4 mole) were mixed, added to a four-necked reaction flask equipped with a stirrer, thermometer, feeder, and reflux condenser, heated to 110°C for 4 hours, and then heated to 170°C for 4 hours. After the reaction, the mixture was cooled to 100°C, and the pH of the system was adjusted to 5.8 with acid. 1000ml of toluene was added to the system twice to extract the reaction solution, the toluene phase was combined, and the toluene was recovered to obtain 569.4g (3.771 mole) of the target product, with a yield of 91.3%.

[0055] The product 569.4g (3.771mo...

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Abstract

The present invention relates to a method capable of using p-methyl phenol as raw material and adopting the processes of esterification, dislocation, oxidation, ring-closing reaction, chlorination and hydrolysis to obtain heliotropin. Its total yield can be up to above 50%.

Description

technical field [0001] The invention relates to a method for preparing jasmonal by using p-cresol as a raw material, belonging to the field of fine chemicals. Background technique [0002] Heliotropine, also known as piperonal, chemical name 3,4-dioxymethylene benzaldehyde (3,4-methylenedioxy benzaldehyde), is a very important synthetic fragrance, and is widely used as a brightener in the electroplating industry It is also a raw material for the synthesis of L-3,4-dihydroxyphenylalanine and alkaloids in the pharmaceutical industry. [0003] At present, the main production method of jasmonal is to use safrole as raw material to obtain jasmonal through isomerization and oxidation. And sassafras oil must be extracted from the trunk and root of sassafras, which causes great damage to valuable forest resources, and also makes this route vulnerable to the restriction of raw material supply, and there are many auxiliary materials and high production costs, especially A large amou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/54
Inventor 蒋文伟李晶晶赖崇伟罗芩杨琴
Owner SICHUAN UNIV
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