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A kind of synthetic method of terminal carboxylic acid

A technology of terminal carboxylic acid and synthesis method, which is applied in the preparation of carboxylic acid ester, the preparation of carboxylic acid by oxidation, chemical instruments and methods, etc., can solve the problems of high reaction temperature and high reaction pressure, and achieve simple steps, energy saving, production high rate effect

Active Publication Date: 2022-03-29
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many problems in these methods, such as the use of toxic carbon monoxide gas reagents, high reaction temperature, and high reaction pressure requirements, and higher requirements are placed on the pressure resistance of the reaction device.

Method used

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  • A kind of synthetic method of terminal carboxylic acid
  • A kind of synthetic method of terminal carboxylic acid
  • A kind of synthetic method of terminal carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 nonanoic acid (structural formula 4-a)

[0040]

[0041] TFPP stands for monophosphine ligand.

[0042]Under argon protection, palladium acetate (0.025mmol, 0.0056g), monophosphine ligand TFPP (0.15mmol, 0.0474g), 0.5mL toluene were successively added to the reactor, and the structural formula was 1-octene of 3-a ( 0.5mmol, 0.0561g), formic acid (0.75mmol, 0.0345g) and acetic anhydride (0.1mmol, 0.0102g). Screw on the bottle cap to seal it, and adjust the temperature of the heating plate to 80°C. Stop heating after 48 hours, cool to room temperature, add 3 mL of dichloromethane and transfer to a 125 mL separating funnel. Add 30 mL of 1M NaOH solution to the mother liquor, and wash with dichloromethane three times, 30 mL each time. The aqueous phase was acidified with 15 mL of 3M hydrochloric acid, and then extracted three times with 30 mL of dichloromethane. Obtain 0.0727g light yellow oily liquid nonanoic acid (see structural formul...

Embodiment 2 13

[0043] The synthesis of embodiment 2 tridecanoic acid (structural formula 4-b)

[0044]

[0045] TFPP stands for monophosphine ligand.

[0046] Under the protection of argon, palladium acetate (0.025mmol, 0.0056g), monophosphine ligand TFPP (0.15mmol, 0.0474g), 0.5mL toluene were successively added into the reactor, and 1-dodecene with the structural formula 3-b (0.5mmol, 0.0842g), formic acid (0.75mmol, 0.0345g) and acetic anhydride (0.1mmol, 0.0102g). Screw on the bottle cap to seal it, and adjust the temperature of the heating plate to 80°C. Heating was stopped after 48 hours, cooled to room temperature, separated by column chromatography (petroleum ether: ethyl acetate volume ratio was 10:1) to obtain 0.0989g white solid tridecanoic acid (see structural formula 4-b described in the above reaction formula ), the yield is 92%, and the ratio of linear chain to branched chain is 25:1

Embodiment 3

[0047] The synthesis of embodiment 3 1-naphthoic acid (structural formula 4-c)

[0048]

[0049] TFPP stands for monophosphine ligand.

[0050] Under the protection of argon, palladium acetate (0.025mmol, 0.0056g), monophosphine ligand TFPP (0.15mmol, 0.0474g), and 0.5mL toluene were successively added to the reactor, and the 1-allyl group with the structural formula 3-c Naphthalene (0.5mmol, 0.0841g), formic acid (0.75mmol, 0.0345g) and acetic anhydride (0.1mmol, 0.0102g). Screw on the bottle cap to seal it, and adjust the temperature of the heating plate to 80°C. Stop heating after 48 hours, cool to room temperature, add 3 mL of dichloromethane and transfer to a 125 mL separating funnel. Add 30 mL of 1M NaOH solution to the mother liquor, and wash with dichloromethane three times, 30 mL each time. The aqueous phase was acidified with 15 mL of 3M hydrochloric acid, and then extracted three times with 30 mL of dichloromethane. Obtain 0.091g of white solid 1-naphthalene ...

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Abstract

The invention discloses a method for synthesizing terminal carboxylic acid, which is characterized in that: under the protection of inert gas, olefin, formic acid, acetic anhydride, Pd(OAc) represented by formula (3) are mixed 2 And the monophosphorus ligand TFPP is added in the organic solvent in proportion, under the condition of 80-90 ℃, the olefin, formic acid and acetic anhydride shown in formula (3) are in the metal palladium salt Pd(OAc) 2 The terminal carboxylic acid shown in the following formula is obtained through the hydrocarbonylation reaction of 48-72h under the catalysis of the monophosphorus ligand TFPP, and the target product terminal carboxylic acid is separated after the reaction is completed; wherein the olefin shown in the formula (3) is selected from cycloalkene or R 1 Straight-chain alkenes that are electron-donating groups. The method of the present invention can react to obtain the corresponding terminal carboxylic acid and its derivatives under mild conditions of low temperature and non-high pressure, and the synthesis method has simple steps, convenient operation, high yield, and can greatly save energy and energy. Improve synthesis efficiency.

Description

technical field [0001] The invention belongs to the field of organic drug synthesis, and in particular relates to a method for synthesizing terminal carboxylic acids. Background technique [0002] Terminal carboxylic acids and their derivatives are very important compounds in organic synthesis, fine chemicals, and medicinal chemistry. They play a huge role in industry as drugs, spices, and synthetic building blocks. [0003] The synthesis of such compounds in industry generally uses toxic, flammable and explosive carbon monoxide gas to react under high temperature and high pressure. However, these methods have problems such as the use of toxic carbon monoxide gas reagents, high reaction temperature, and high reaction pressure requirements, and higher requirements are placed on the pressure resistance of the reaction device. The present invention thus provides a method for synthesizing terminal carboxylic acids by using a catalyst. Contents of the invention [0004] In vi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/16C07C53/126C07C57/40C07C57/30C07C53/19C07C59/125C07C59/147C07D317/30C07C55/16C07C69/34C07C67/313
CPCC07C51/16C07D317/30C07C67/313C07C53/126C07C57/40C07C57/30C07C53/19C07C59/125C07C59/147C07C55/16C07C69/34
Inventor 史一安任文龙储健骁孙飞
Owner CHANGZHOU UNIV