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ChemicalBook CAS DataBase List METHYL ABIETATE
127-25-3

METHYL ABIETATE synthesis

8synthesis methods
Prepared by esterification of wood rosin with methanol.
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Yield: 99.6%

Reaction Conditions:

with lithium hydroxide monohydrate in N,N-dimethyl-formamide at 93 - 100;Inert atmosphere;Reagent/catalyst;Concentration;

Steps:

1 Example 4
In the reaction, is I abietic acid, dimethyl carbonate representative II, III is methyl ester of abietic acid product. In the is provided with a stirrer, thermometer and reflux condenser of the 250 ml adding three-necked bottle 30 ml DMF organic solvent, then adding the abietic acid (0.05mol, 15 . 0g) and methyl esterification reagent dimethyl carbonate C3H6O3(0.5mol, 45 . 0g), alkali catalyst lioh LiOH·H2O (0.1mol, 4 . 2g), the abietic acid, dimethyl carbonate, lithium hydroxide dissolved in DMF, under the protection of nitrogen 100 °C return to stable heating in oil bath, that is, when the dropping the internal reflux three-necked bottle 1-2 drop/sec is stable, the stable reflow temperature to reflux temperature of 93 °C. Every 1h tracking of the reaction progress by thin-layer chromatography, until detecting three-necked bottle no reaction raw material, the end of the reaction, the reaction a total 46h. After the reaction, the reaction of the substance is poured into 600 ml of deionized water in a beaker, with 3.5% hydrochloric acid solution to adjust pH to neutral, then using 50 ml dichloromethane extraction, takes organically, then the remaining aqueous phase dichloromethane is used for extraction, the extraction is repeated a total of 3 times, the merger 3 times the resulting organic phase, extraction by adding deionized water washing, separating the organic layer and drying with anhydrous sodium sulfate, after drying by rotary evaporator to obtain the product reducing the dichloromethane, the crude product of methyl ester of abietic acid. The liquid phase of the crude product is used for detecting the content of the methyl ester of abietic acid. Finally the crude product of methyl ester of abietic acid concentrate under reduced pressure to dry, purify by column chromatography (silica gel column 300-400 mesh, the composition is 100% petroleum ether, gradient elution) methyl ester of abietic acid product 15.6g, yield of 99.6%.

References:

Guangxi University;Zhang, Min;Xiang, Pei;Mo, Jing;Lan, Qing;Zhang, Yan CN105712875, 2016, A Location in patent:Paragraph 0022; 0023; 0024; 0025; 0026; 0027; 0028-0032

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