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Method for the deacylation and/or dealkylation of compounds

A dealkylation and deacylation technology, applied in the field of chemical compounds, can solve the problems of undisclosed C-dealkylation, undisclosed or even proposed high-pressure conditions, etc.

Pending Publication Date: 2020-08-14
UNIVERSITY OF ANTWERP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although Yang et al. (2013 (Journal of Molecular Catalysis A: Chemical 368-369 (2013) 61-65)) disclosed a method for converting guaiacol to catechol in high-temperature water, it did not disclose or even bring up high pressure conditions
Furthermore, Yang et al. (2013) did not disclose the C-dealkylation of the compound

Method used

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  • Method for the deacylation and/or dealkylation of compounds
  • Method for the deacylation and/or dealkylation of compounds
  • Method for the deacylation and/or dealkylation of compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0282] Example 1: Synthesis of Catechol [JBO-334] by Eugenol (4-allyl-2-methoxyphenol)

[0283] This experiment was performed according to General Method A. Eugenol (164 mg, 1 mmol) was used as substrate, concentrated H 2 SO 4 (11μL, 0.2mmol, 0.2 equivalents) used as acidic catalyst, H 2 O (2 mL) was used as solvent. Reacted at 50 bar N 2 3 h at 250 °C under pressure. Catechol was obtained in 73% isolated yield (80 mg, 0.73 mmol). 1 H NMR (400MHz, CDCl 3 ): δ6.90-6.85 (m, 2H), 6.83-6.81 (m, 2H), 5.10 (s, 2H) ppm. 13 C NMR (101MHz, CDCl 3 ): δ 143.7 (C), 121.5 (CH), 115.7 (CH) ppm. HRMS(ESI), for C 6 h 7 o 2 [M+H] + , the calculated value is 111.0446, and the measured value is 111.0447.

Embodiment 2

[0284] Example 2: Synthesis of catechol [JBO-307] by isoeugenol (2-methoxyl-4-prop-1-enylphenol)

[0285] This experiment was performed according to General Method A. Isoeugenol (164 mg, 1 mmol) was used as substrate, concentrated HCl (17 μL, 0.2 mmol, 0.2 equiv) was used as acidic catalyst, H 2 O (2 mL) was used as solvent. Reacted at 50 bar N 2 3 h at 250 °C under pressure. Catechol was obtained in 85% isolated yield (94 mg, 0.85 mmol).

Embodiment 3

[0286] Example 3: Synthesis of catechol [JBO-487] by o-eugenol (6-allyl-2-methoxyphenol)

[0287] This experiment was performed according to General Method A. O-eugenol (164 mg, 1 mmol) was used as substrate, concentrated H 2 SO 4 (56μL, 1mmol, 1 equivalent) used as acidic catalyst, H 2 O (2 mL) was used as solvent. Reacted at 50 bar N 2 3 h at 250 °C under pressure. Catechol was obtained in 18% NMR yield (0.18 mmol).

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Abstract

The present invention in general relates to a method for the deacylation and / or dealkylation (both O-dealkylation as well as C-dealkylation) of compounds, more specifically of aromatic compounds. Themethod is characterized by contacting the compound with an acid-containing aqueous reaction mixture using high temperature and high pressure conditions. The invention also provides a method for preparing a compound suitable for further deacylation using the method of the invention.

Description

[0001] field of invention [0002] The present invention relates generally to processes for the deacylation and / or dealkylation (O-dealkylation and C-dealkylation) of compounds, more particularly aromatic compounds. The process is characterized by contacting the compound with an aqueous acid-containing reaction mixture using conditions of elevated temperature and pressure. The invention also provides methods for preparing compounds suitable for further deacylation using the methods of the invention. [0003] Background of the invention [0004] Several methods for the O-dealkylation of aromatics have been described. For example US 2.100.228 discloses the dealkylation of aryl alkyl ethers, in particular the dealkylation of guaiacol to pyrocatechol. According to this method, an arylalkyl ether is heated to a typical temperature of about 140-200°C in the presence of an aliphatic amine hydrohalide while passing a hydrohalic acid such as HCl or HBr through the reaction mixture unt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/055C07C37/50C07C37/52C07C39/04C07C39/08C07C39/10C07C51/367C07C59/52C07C41/16C07C43/205C07C45/28C07C49/84
CPCC07C37/055C07C37/50C07C37/52C07C41/16C07C45/28C07C51/367C07C39/08C07C39/04C07C39/10C07C59/52C07C43/2055C07C49/84
Inventor B·梅斯J·邦蒙S·瑟尔吉瓦E·布朗迪奥克斯
Owner UNIVERSITY OF ANTWERP