2-[(4-dodecyloxy phenyl) sulfuryl] butyric acid synthetic method

A technology of dodecyloxyphenyl and sodium dodecyloxybenzene sulfinate, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problem of poor production economy and poor process safety , expensive raw materials and other problems, to achieve the effect of reducing production costs, improving synthesis efficiency, and simple post-processing

Active Publication Date: 2015-03-11
江西扬帆新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantages of this synthetic process route are expensive raw materials used, poor process safety, large amount of waste water, and poor production economy.

Method used

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  • 2-[(4-dodecyloxy phenyl) sulfuryl] butyric acid synthetic method
  • 2-[(4-dodecyloxy phenyl) sulfuryl] butyric acid synthetic method
  • 2-[(4-dodecyloxy phenyl) sulfuryl] butyric acid synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1, a kind of synthetic method of 2-[(4-dodecyloxyphenyl) sulfone group] butanoic acid, carries out following steps successively:

[0055] 1), the raw material phenol (0.2mol), bromododecane (0.2mol), potassium carbonate (0.2mol) and sodium chloride (0.02mol) were refluxed in 100ml methyl ethyl ketone and reacted for 4 hours. Ketone, the obtained residual liquid was filtered, and the obtained filtrate (organic phase) was distilled under reduced pressure (5-6 Torr), and the fraction at 168-172 ° C was collected to obtain 48.3 g (0.184 mol) of dodecylphenyl ether, with a yield of 92.2% , 98.1% purity.

[0056] 2) Dissolve the dodecylphenyl ether (0.184mol) obtained in step 1) in 300mL of dichloromethane, add sodium chloride (0.37mol) and mix, keep the reaction temperature at 5°C, and slowly add it dropwise (30min to finish) Chlorosulfonic acid (0.74mol) insulation reaction 4h, then the reaction liquid that obtains is added the mixture of 800g ice and saturated ...

Embodiment 2

[0060] Embodiment 2, a kind of synthetic method of 2-[(4-dodecyloxyphenyl) sulfone group] butanoic acid, carries out following steps successively:

[0061] 1), reflux the raw materials phenol (0.3mol), chlorododecane (0.2mol), sodium carbonate (0.4mol) and potassium chloride (0.1mol) in 100ml cyclohexanone for 2h, evaporate after the reaction Cyclohexanone, the resulting residual liquid was filtered, the obtained filtrate (organic phase) was distilled under reduced pressure, and the fraction at 168-172 ° C was collected to obtain 47.3 g (0.18 mol) of dodecylphenyl ether, with a yield of 90.1% and a purity of 97.1 %.

[0062] 2) After dissolving the dodecylphenyl ether (0.18mol) obtained in step 1) in 300mL of dichloromethane, add sodium chloride (0.36mol) to mix, keep the reaction temperature at 20°C, and slowly add it dropwise (about 30min to finish) ) chlorosulfonic acid (0.54mol) insulation reaction 3h, then the reaction solution obtained is added to the mixture of 800g ic...

Embodiment 3

[0066] Embodiment 3, a kind of synthetic method of 2-[(4-dodecyloxyphenyl) sulfone group] butanoic acid, carries out following steps successively:

[0067] 1), the raw material phenol (0.24mol), iodododecane (0.2mol), potassium carbonate (0.6mol) and sodium bromide (0.04mol) were refluxed in 100ml cyclohexane for 6 hours, and evaporated after the reaction Cyclohexane, the resulting residual liquid was filtered, the obtained filtrate (organic phase) was distilled under reduced pressure, and the fraction at 168-172 ° C was collected to obtain 45.7 g (0.174 mol) of dodecylphenyl ether, with a yield of 87.1% and a purity of 98.1 %.

[0068] 2), after dissolving the dodecylphenyl ether (0.174mol) obtained in step 1) in 300mL of dichloromethane, add sodium chloride (0.02mol) and mix, keep the reaction temperature at 10°C, slowly drop (about 30min) ) chlorosulfonic acid (0.35mol) insulation reaction 6h, then the reaction solution obtained is added to the mixture of 800g ice and satu...

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Abstract

The present invention discloses a 2-[(4-dodecyloxy phenyl) sulfuryl] butyric acid synthetic method which comprises the following steps: 1), reflux reaction of phenol, halogenated dodecane, an inorganic acid binding agent and an inorganic salt in organic solvent I to obtain dodecyl benzene ether; 2), reaction of the dodecyl benzene ether, sodium chloride and chlorosulfonic acid in dichloromethane to obtain 4-dodecyloxy benzene sulfonyl chloride; 3), reduction reaction of the 4-dodecyloxy benzene sulfonyl chloride, a reducing agent and a pH regulator in a mixture of water and organic solvent II to obtain 4-dodecyloxy benzene sulfinic acid sodium salt; 4), reflux reaction of the 4-dodecyloxy benzene sulfinic acid sodium salt, halogenated butyric acid methyl ester and a catalyst in methanol, then filtration of reaction liquid to obtain filtrate; 5), mixing of the filtrate and an aqueous sodium hydroxide solution for reaction to finally obtain 2-[(4-dodecyloxy phenyl) sulfuryl] butyric acid.

Description

technical field [0001] The invention relates to a synthesis method of an organic compound 2-[(4-dodecyloxyphenyl)sulfone group]butanoic acid. Background technique [0002] 2-[(4-Dodecyloxyphenyl)sulfone]butanoic acid, which has the formula C 22 h 36 o 5 S, its structural formula is shown in S-1, and its pure product is a white solid. As an important organic intermediate of a new type of cyan coupler, the compound is widely used in the fields of organic synthesis, color photosensitive materials, printing and the like. [0003] [0004] The synthetic technique of 2-[(4-dodecyloxyphenyl) sulfone group] butanoic acid is as follows at present: [0005] According to the literature (Dyes and Dyeing, 2011, (2), 1-4), it is reported that p-hydroxyphenol and methyl bromobutyrate are used as raw materials to generate sulfides through nucleophilic substitution reactions under alkaline conditions. Oxidation forms a sulfone group, and then synthesizes the target product through an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/44C07C315/04C07C315/00
Inventor 樊彬时云龙李桂芹吕雪皓
Owner 江西扬帆新材料有限公司
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