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Synthesis method of 5-oxa-nonanedioic acid

A synthetic method, the technology of azelaic acid, which is applied in chemical instruments and methods, preparation of carboxylate salts, preparation of organic compounds, etc., can solve problems such as the lack of effective synthesis methods, and achieve high product yield, high product purity, and reaction The effect of mild conditions

Inactive Publication Date: 2020-01-03
上海吉奉生物科技有限公司 +1
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Problems solved by technology

[0004] The purpose of this invention is to provide a kind of synthetic method of 5-oxazelaic acid, mainly solve the technical problem that its effective synthetic method lacks

Method used

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Experimental program
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Embodiment

[0012] step 1:

[0013] Add KOH (59.0 g, 1.05 mol), DMSO (680 mL) and 1,4-butanediol (63.0 g, 0.70 mol) into a 1-liter four-neck flask, start stirring, and add 4-bromobutylbenzyl under nitrogen protection Ether (34.0 g, 0.14 mol), react at room temperature for 1 hour. The reaction solution was quenched by pouring into water (6.8 L), extracted with dichloromethane (1.7 L×2); the organic phases were combined, washed with saturated brine (1 L×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried. The crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate volume ratio = 5:1) to obtain high-purity compound 1 (29.0 g, 11.5 mmol, 82.2%). 1 H NMR (400 MHz, CDCl 3 ): 7.40-7.23 (m, 5H), 4.50 (s, 2H), 3.65-3.60 (m, 2H), 3.52-3.41 (m,6H), 1.74-1.60 (m, 8H) ppm.

[0014] Step 2:

[0015] Add compound 1 (16.4 g, 58.5 mmol), methanol (330 mL), Pd / C (0.82 g, wet Pd / C with 50% water content, Pd content is 10% by weight o...

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Abstract

The invention relates to a synthesis method of 5-oxa-nonanedioic acid, and mainly solves the technical problem of lack of effective synthesis methods of 5-oxa-nonanedioic acid. The synthesis method provided by the invention comprises the following steps: under protection of nitrogen, adding 4-bromobutyl benzyl ether into a dimethylsulfoxide (DMSO) solution of 1,4-butanediol and potassium hydroxideto generate a compound 1; carrying out catalytic debenzylation on the compound 1 by Pd / C in methanol in a hydrogen environment to generate a compound 2; and oxidizing the compound 2 by a Jones reagent in acetone to produce a target compound 3. The reaction formula is as follows. The synthesis method has the advantages of short reaction time, mild reaction, high product purity and high yield.

Description

technical field [0001] The invention relates to a synthesis method of 5-oxazelaic acid. Background technique [0002] 5-oxazelaic acid (CAS: 7423-25-8) is mainly used as a building block for the synthesis of small organic molecules; at the same time, it has also been widely studied in the field of plasticizers. At present, there are few reports about the synthesis of this compound, and the main synthetic routes are: [0003] Otto Meth-Cohn et al. reported in the Journal of the Chemical Society (Journal of the Chemical Society -Perkin Transactions 1,1997,21,3197-3204), using bis(3-chloropropyl) ether as raw material, 90°C in DMSO solution with Sodium cyanide reacts to generate 4-(3-cyanopropoxy)-butyronitrile; then Rhodococcus AJ270 is used to hydrolyze 4-(3-cyanopropoxy)-butyronitrile into 5-oxazelaic acid. Nishigori (Kobunshi Kagaku, 1951, 8,249), German patent 919167, etc. use γ-butyrolactone as raw material, mix it with potassium hydroxide at 120-130°C, and then heat an...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C41/26C07C43/178C07C43/13C07C51/305C07C59/305
CPCC07C41/16C07C41/26C07C51/305C07C43/1785C07C43/132C07C59/305
Inventor 徐红岩张志文
Owner 上海吉奉生物科技有限公司
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