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Method for preparing 2,2-dialkyl-5-hydroxymethyl-1,3-dioxanes compounds

A technology for dioxane and ester compounds, which is applied in 2 fields, can solve problems such as complicated and difficult operations, and achieve the effects of simple process, high industrial application value and convenient operation

Inactive Publication Date: 2009-04-01
SHANGHAI CHEMPARTNER CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the prior art synthesis of 2,2-dialkyl-5-hydroxymethyl-1,3-dioxane compounds using flammable and explosive reagents to make the operation complicated difficult problem, and provide a preparation method that does not require sensitive reagents, has simple process, is convenient to operate, and is easy to apply to large-scale industrial production

Method used

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  • Method for preparing 2,2-dialkyl-5-hydroxymethyl-1,3-dioxanes compounds
  • Method for preparing 2,2-dialkyl-5-hydroxymethyl-1,3-dioxanes compounds
  • Method for preparing 2,2-dialkyl-5-hydroxymethyl-1,3-dioxanes compounds

Examples

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Embodiment 1

[0020] In a 250 ml three-necked bottle, a thermometer and a stirrer were installed, and the carboxylate (R 1 =R 2 =R 3 =methyl, 0.1mol), THF (100ml), NaBH 4 (0.1 mol), heated to 40°C. Then calcium chloride (0.02mol) in water (50ml) was slowly added dropwise for 3 hours. Then, it was further heated and stirred for 4 hours (GC tracking). It was then filtered and extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the product obtained by distillation was a colorless liquid with a yield of 85% and a purity of 98.6% (GC).

Embodiment 2

[0022] In a 250 ml three-necked bottle, a thermometer and a stirrer were installed, and the carboxylate (R 1 =R 2 =R 3 = n-propyl, 0.1mol), 1,4-dioxane (80ml), NaBH 4 (0.2mol), heated to 50°C. Then calcium bromide (0.04mol) in water (50ml) was slowly added dropwise for 4 hours. Then, it was further heated and stirred for 2 hours (GC tracking). It was then filtered and extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the product obtained by distillation was a colorless liquid with a yield of 92% and a purity of 98.2% (GC).

Embodiment 3

[0024] In a 250 ml three-necked bottle, a thermometer and a stirrer were installed, and the carboxylate (R 1 =R 2 =R 3 = n-butyl, 0.1mol), n-butyl ether (70ml), NaBH 4 (0.3mol), heated to 60°C. Then calcium fluoride (0.05mol) in water (50ml) was slowly added dropwise for 4 hours. Then, it was further heated and stirred for 4 hours (GC tracking). It was then filtered and extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the product obtained by distillation was a colorless liquid with a yield of 88% and a purity of 99.1% (GC).

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Abstract

The invention discloses a method used for preparing a 2, 2-dialkyl-5-methylol-1, 3-dioxane compound shown in formula B. The method is as follows: a carboxylicacidesters compound and a reducer, MBH4, shown in the formula A are added into a protons solvent, M represents Li, Na or K, and the aqueous solution of calcium salt is added into the solvent for reaction; wherein, R1 represents methyl, ethyl, n-propyl, n-butyl or phenyl; R2 represents hydrogen, methyl, ethyl, n-propyl, n-butyl or phenyl; or the R1 and R2 are connected into straight-chain butylidene or straight-chain amylidene; R3 represents methyl, ethyl, n-propyl, n-butyl or benzyl. The method of the invention is simple; the operation is convenient; the yield is high; the method is suitable for large-scale industrial production, with comparatively high industrial application value.

Description

technical field [0001] The invention relates to the field of synthesis and preparation of organic compounds, in particular to a preparation method of 2,2-dialkyl-5-hydroxymethyl-1,3-dioxane compounds. Background technique [0002] In recent years, 2,2-dialkyl-5-hydroxymethyl-1,3-dioxane compounds have been widely used as branched side chains in the synthesis of polymer dendrimers. In addition, in the study of active targeted drug synthesis, it is necessary to synthesize this side chain as a bridge, so that two drug molecules can be carried on one carrier to achieve the effect of killing two birds with one stone. Therefore, the synthesis and preparation of 2,2-dialkyl-5-hydroxymethyl-1,3-dioxane compounds has been highly valued. [0003] In the prior art, the main synthesis methods of 2,2-dialkyl-5-hydroxymethyl-1,3-dioxane compounds are: [0004] Gaudry (Synthesis of 5,5'-dihydroxyleucine and 4-fluoro 5,5'-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06
Inventor 刘国斌李原强刘军屈博磊
Owner SHANGHAI CHEMPARTNER CO LTD