ChemicalBook CAS DataBase List Nordihydroguaiaretic acid

Nordihydroguaiaretic acid synthesis

3synthesis methods

Product Name:Nordihydroguaiaretic acid
CAS Number:500-38-9
Molecular formula:C18H22O4
Molecular Weight:302.36

Nordihydroguaiaretic acid is obtained by hydrodemethylation of dimethyl ether of guaiacolinic acid, a component of guaiac resin. It is also produced from desert plant, creosote bush (Larrea divaricata Cav. Or Corillea tridentate), which can be widely found in the border zone of southern of USA and northern of Mexico.

5701-82-6 Synthesis

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500-38-9
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Yield:500-38-9 91.26%

Reaction Conditions:

with hydrogen bromide in water at 126; for 10 h;Inert atmosphere;Reagent/catalyst;

Steps:

6.1; 6.2 Method 1:
Add 17.92g (50mmol) of 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane to the reaction flask, add 47percent hydrobromic acid under nitrogen protection 110 mL (951 mol) of aqueous solution, sealed reaction device, heated to 126°C for 10 hours under magnetic stirring.Then the reaction device was released from airtight, cooled to 05 and stirred overnight, diluted with 300mL water under stirring, the precipitated solid was suction filtered, the filter cake was washed with 50mL water, recrystallized with 45percent acetic acid to obtain needle-like crystals, heated to 65 It was dried under reduced pressure for 4 hours to obtain 13.80 g of product with a yield of 91.26percent and a melting point of 184-185°C.The purity determined by HPLC was 99.3percent.

References:

Jincheng Tiancheng Kechuang Co., Ltd.;Su Guiping CN111205171, 2020, A Location in patent:Paragraph 0039-0044

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63-91-2 Synthesis