One-pot method used for synthesis of diaryl methyl ketal

A technology for diaryl methyl ketals and ketals, which is applied to the field of one-pot synthesis of diaryl methyl ketals, can solve problems such as not meeting the requirements of green manufacturing, and achieves the advantages of short steps, good practicability and simple post-processing. Effect

Active Publication Date: 2019-11-01
SOUTHEAST UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology allows for efficient chemical reactions between different types of aniline compounds without generating harmful byproducts like hydrogen fluoroformic acid (HF) which could pollute our airways if released into nature during industrial manufacturing processes.

Problems solved by technology

This patented technical solution describes methods for producing various types of diphenylethanols called monoaromatics like diazene-2-carbonitriles. These compounds contain multiple rings connected at one end but only certain atoms contribute towards their activity. However, they cannot form regular arrangements due to stereochemistry issues during polymerization processes. To solve this issue, different techniques were developed including solvent exchange method, solid state transition metal chemisorption technique, ammonium salt reduction process, and other synthetic procedures involving strong acids and bases.

Method used

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  • One-pot method used for synthesis of diaryl methyl ketal

Examples

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Effect test

Embodiment 1

[0024] Embodiment one: the synthesis of 1-(dimethoxy-phenyl-methyl)-4-methoxy-benzene

[0025]

[0026] 250mL four-necked flask with magnetic stirring, thermometer and reflux condenser, successively added trifluoroacetic anhydride (42.0g, 200mmol), anisole (13.0g, 120mmol), boron trifluoride etherate complex (1.42g, 10mmol ), benzoic acid (12.2 g, 100 mmol) was added in portions, and the temperature was raised to 30-40° C. for 6 hours under stirring to obtain a dark brown solution. Cool down to room temperature, add methanol (60mL) and trimethyl orthoformate (31.8g, 300mmol), the color of the solution turns light red, heat up to 55-60°C for 18h, and add triethylamine (2.0g) after cooling down The pH was adjusted to alkaline, and the color of the solution further became pale yellow. Concentrate under reduced pressure to remove most of the solvent, and a solid precipitates. Add heptane (50mL) to make a slurry, filter, and air-dry at 40°C to obtain white 1-(dimethoxy-phenyl-m...

Embodiment 2

[0027] Embodiment two: the synthesis of 1-(dimethoxy-phenyl-methyl)-4-isopropyl-benzene

[0028]

[0029] 250mL four-necked flask with magnetic stirring, thermometer and reflux condenser, successively added trifluoroacetic anhydride (42.0g, 200mmol), cumene (14.4g, 120mmol), boron trifluoride diethyl ether complex (1.42g, 10mmol ), benzoic acid (12.2g, 100mmol) was added in portions, and the temperature was raised to 30-40° C. for 4 hours under stirring to obtain a wine-red solution. Cool down to room temperature, add methanol (60mL) and trimethyl orthoformate (31.8g, 300mmol), the color becomes light yellow, heat up to 55-60°C for 18h, add triethylamine (2.0g) to adjust the temperature When the pH becomes alkaline, the color of the solution becomes lighter. Concentrate under reduced pressure to remove most of the solvent, add dichloromethane (60mL) to dissolve, wash twice with water (30mL*2), collect the organic layer, concentrate under reduced pressure to obtain an oily ...

Embodiment 3

[0030] Embodiment three: the synthesis of 2-chloro-5-[dimethoxy-(4-methoxy-phenyl)-methyl]-thiophene

[0031]

[0032] 250mL four-necked flask with magnetic stirring, thermometer and reflux condenser, successively added trifluoroacetic anhydride (42.0g, 200mmol), anisole (16.2g, 150mmol), boron trifluoride diethyl ether complex (2.13g, 15mmol ), 5-chloro-2-thiophenecarboxylic acid (16.3 g, 100 mmol) was added in portions, and the temperature was raised to 30-40° C. for 5 hours under stirring to obtain a deep reddish-brown solution. Cool down to room temperature, add methanol (60 mL) and trimethyl orthoformate (31.8 g, 300 mmol), the color change is not obvious. Reheat to 55-60°C and keep it warm for 24 hours. After cooling down, add triethylamine (3.0 g) to adjust the pH to alkaline, concentrate most of the solvent to obtain a reddish-brown oil, add dichloromethane (80 mL) to dissolve, and water ( 40mL*2) washed twice, collected the organic layer, concentrated under reduce...

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Abstract

The invention discloses a one-pot method used for synthesis of diaryl methyl ketal. The on-pot method is shorter in process, and is more effective. A novel synthesis strategy is provided for synthesisof some complex diaryl ketones. According to the one-pot method, an aryl carboxylic acid and a R-substituted benzene compound are selected, in the presence of trifluoroactic anhydride, boron trifluoride diethyl etherate is taken as a catalyst, direct acylation reaction is carried out, without treatment, methanol and trimethyl orthoformate are added for continuous reaction so as to obtain a diarylmethyl ketal product, so that one-pot synthesis of diaryl methyl ketal from aromatic acids is realized.

Description

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Claims

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Application Information

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Owner SOUTHEAST UNIV
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