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Method for preparing 3,4-methylenedioxophenyl-2-acetone from benzofuranol side product used as raw material

A methylene dioxyphenyl and furan phenol technology, which is applied in directions such as organic chemistry, can solve the problems of lack of sassafras oil resources, unfriendly environment and high cost of raw materials, and achieves the effects of low production cost, simple process and high content

Inactive Publication Date: 2013-09-25
JIANGSU SANJILI CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The industrial production of 3,4-methylenedioxyphenyl-2-propanone mainly uses safrole as raw material, which is extracted from the roots and trunks of sassafras trees. The main raw material origins in the world are China and Vietnam. Due to the impact of the wave of ecological protection and forest protection policies, traditional sassafras oil resources are increasingly scarce, and the route of synthesizing 3,4-methylenedioxyphenyl-2-propanone from safrole is restricted by raw materials , while other synthetic routes all have the disadvantages of high cost of raw materials, unfriendly to the environment, etc.
[0016] At present, catechol is used as raw material to produce furanol in China, and the annual output is about 6,000 tons, and its main by-product 4-(2-methallyl)-1,2-benzenediol is about 700 tons. For downstream products, the manufacturer does not separate it from the residual liquid of the rectification tank, but only treats it as heavy oil fuel, with low added value

Method used

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  • Method for preparing 3,4-methylenedioxophenyl-2-acetone from benzofuranol side product used as raw material
  • Method for preparing 3,4-methylenedioxophenyl-2-acetone from benzofuranol side product used as raw material
  • Method for preparing 3,4-methylenedioxophenyl-2-acetone from benzofuranol side product used as raw material

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Experimental program
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Effect test

Embodiment 1

[0032] Under nitrogen protection, 30mL of water and 26.1g (0.15mol) of dibromomethane were refluxed. Mix 16.4g (0.10mol) 4-(2-methylallyl)-1,2-benzenediol and 10.0g (0.25mol) sodium hydroxide in 50mL water evenly, add after 2h, reflux for 2h, liquid Control the reaction in phase chromatography, cool after the reaction, add 100mL ethyl acetate for layering, wash the organic layer with 2% sodium hydroxide solution, dry, and distill to obtain 15.0g of light yellow liquid 5-(2-methallyl)benzene And[d][1,3]dioxole, content 98.3%, yield 83.4%. 1 H NMR (CDCl 3 , 300MHz) δ: 1.67(t, J=1.2Hz, 3H, CH 3 ), 3.23 (s, 2H, ArCH 2 ), 4.73(q, J=1.2Hz, 1H, C=CH), 4.79~4.80(q, J=1.2Hz, 1H, C=CH), 5.93(s, 2H, OCH 2 O), 6.63 ~ 6.75 (m, 3H, C 6 h 3 ).GC-MS(m / z):176(M + ), 151, 131, 103, 77.

Embodiment 2

[0034] Under nitrogen protection, 30mL of water and 17.4g (0.1mol) of dibromomethane were refluxed. Mix 16.4g (0.10mol) 4-(2-methylallyl)-1,2-benzenediol and 8.8g (0.22mol) sodium hydroxide in 50mL water evenly, add after 2h, reflux for 2h, liquid Control the reaction in phase chromatography, cool after the reaction, add 100mL of ethyl acetate for layering, wash the organic layer with 2% sodium hydroxide solution, dry, and distill to obtain 15.5g of light yellow liquid 5-(2-methallyl)benzene And[d][1,3]dioxole, content 97.9%, yield 85.7%.

Embodiment 3

[0036]Under nitrogen protection, 30mL of water and 34.8g (0.20mol) of dibromomethane were refluxed. Mix 16.4g (0.10mol) 4-(2-methylallyl)-1,2-benzenediol and 12.0g (0.30mol) sodium hydroxide in 50mL water evenly, add after 2h, reflux for 2h, liquid Control the reaction in phase chromatography, the reaction is complete; cool, add 100mL ethyl acetate to separate layers, wash the organic layer with 2% sodium hydroxide solution, dry, and distill to obtain 14.7g of light yellow liquid 5-(2-methylallyl) Benzo[d][1,3]dioxole, content 99.0%, yield 82.1%.

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Abstract

The invention discloses a method for preparing 3,4-methylenedioxophenyl-2-acetone from a benzofuranol side product, namely, 4-(2-methylallyl)-1,2-dihydroxybenzene which is used as a raw material and is from the residue in a benzofuranol rectifying still, and the method can be used for solving the problem of utilizing the resource of the benzofuranol side product, namely, the 4-(2-methylallyl)-1,2-dihydroxybenzene. The content of the obtained 3,4-methylenedioxophenyl-2-acetone is 98.3-99.5%, the total yield reaches 71.0-85.7%, and the problems of high production cost, environment pollution and the like of other methods using safrole as a raw material are solved. Equation is shown in the specification.

Description

technical field [0001] The invention relates to a method for preparing 3,4-methylenedioxyphenyl-2-propanone by using furanol by-products as raw materials. Background technique [0002] 3,4-Methylenedioxphenyl-2-propanone, the English name is 3,4-Methylenedioxphenyl-2-propanone. It is an important high-value pharmaceutical intermediate: it is an important raw material for the synthesis of LY300164, a drug for the treatment of epilepsy and neurodegenerative diseases; it is also an important intermediate for the synthesis of α-methyldopa, a drug for the treatment of hypertension; it is also an important synthetic antibacterial firefighting agent Important intermediates of berberine and new anti-tumor drugs. Its molecular structural formula: [0003] [0004] The currently reported methods mainly include the following: safrole method, 3,4-methylenedioxybenzaldehyde method, and 3,4-methylenedioxybenzylamine method. [0005] US4731482 discloses a method for obtaining 3,4-met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/54
Inventor 王宇罗先福毛春晖陈明臧阳陵
Owner JIANGSU SANJILI CHEM
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