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2-(4-methoxycarbonylmethylphenoxymethyl)benzoic acid methyl ester and method for producing the same

A technology of methoxycarbonylmethylphenoxymethyl and methyl chloromethyl benzoate, applied in the field of methyl 2-benzoate and its manufacture, to achieve the effects of energy saving and easy steam heating

Inactive Publication Date: 2009-08-12
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, even in this method, the use of solvents, peroxides, expensive halogenating agents, etc. becomes a limitation in industrial practice, and there are many problems

Method used

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  • 2-(4-methoxycarbonylmethylphenoxymethyl)benzoic acid methyl ester and method for producing the same
  • 2-(4-methoxycarbonylmethylphenoxymethyl)benzoic acid methyl ester and method for producing the same
  • 2-(4-methoxycarbonylmethylphenoxymethyl)benzoic acid methyl ester and method for producing the same

Examples

Experimental program
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Embodiment 1

[0065] Example 1: Production of methyl 2-(4-methoxycarbonylmethylphenoxymethyl)benzoate through the production of methyl 2-chloromethylbenzoate

[0066] [Process 1]

[0067] 643ml of xylene, 134.1g (1.0mol) of benzofuranone, 18.2g (0.08mol) of benzyltriethylammonium chloride and BF 3 - Ether complex 9.9 g (0.07 mol), heated to 100°C. Next, 142.8 g (1.2 mol) of thionyl chloride was dripped over 1 hour, and it stirred at 125-132 degreeC for 2 hours further. Xylene and excess thionyl chloride (about 350 ml) were distilled off under normal pressure until the internal temperature reached 135°C, and xylene (about 350 ml) was further distilled off under reduced pressure.

[0068] [Process 2]

[0069] To the concentrated residue obtained in Step 1, 80.1 g (2.5 mol) of methanol was added dropwise over 1 hour. During this period, cool with a water bath to keep the internal temperature below 60°C. Stirring was then carried out at 50°C for 1 hour and cooled to 25°C.

[0070] Then, t...

Embodiment 2

[0077] Example 2: (11-oxo-6,11-dihydrodibenzo[b,e]oxa Manufacture of -2-yl)acetic acid

[0078] The whole amount of 2-(4-methoxycarbonylmethylphenoxymethyl) methyl benzoate obtained in Example 1 is packed into a four-necked flask, and 17.0 g of sodium hydroxide is dissolved in water 100 ml of the obtained solution and 150 ml of methanol were stirred at 65° C. for 2 hours.

[0079] Then cool to room temperature (about 25° C.), then dilute with 200 ml of water, then add 2.0 g of activated carbon and stir at room temperature for 1 hour, filter with a Buchner funnel to separate the activated carbon, and wash the mixture with 100 ml of water on a Buchner funnel. activated carbon. A solution obtained by dissolving 26.5 g of acetic acid in 50 ml of water was added dropwise to a solution obtained by dissolving the filtered mother liquor and washing liquid at 60° C. over 2 hours, and crystals were precipitated at the same temperature. Next, after cooling to 10° C., the crystals wer...

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Abstract

Disclosed is a method for producing 2-(4-methoxycarbonylmethylphenoxymethyl)benzoic acid methyl ester by reacting 2-chloromethylbenzoic acid methyl ester and 4-hydroxyphenylacetic acid methyl ester. A dibenzooxepinacetic acid useful as an intermediate for pharmaceutical products can be advantageously produced through this method for producing 2-(4-methoxycarbonylmethylphenoxymethyl)benzoic acid methyl ester.

Description

technical field [0001] The present invention relates to 2-(4-methoxycarbonylmethylphenoxymethyl) methyl benzoate and its preparation method. Background technique [0002] A method for producing olopatadine (olopatadine), which is useful as an antiallergic drug, is disclosed in Japanese Unexamined Patent Application Publication No. 6-9609. Acetic acid (dibenzoxepinacetic acid) produces olopatadine with the following reaction process shown in the flow chart. [0003] [0004] Dibenzoxa Acetic acid is produced by ring-closing 2-(4-methoxycarbonylmethylphenoxymethyl)benzoic acid or its ethyl ester produced from benzofuranone or 2-methylbenzoic acid, for example, in The production method thereof is disclosed in JP-A-6-9609 and US Patent No. 4,082,850. [0005] The preparation method of the ester of 2-(4-carboxymethylphenoxymethyl)benzoic acid described in JP-A-6-9609 is the method shown in the following flow chart, using The methyl ester was 1.62 times the molar amount o...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/76C07D313/12C07B61/00
CPCC07C69/76C07C67/14C07D313/12C07C67/31
Inventor 桂正林健人田中正英
Owner SUMITOMO CHEM CO LTD