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ChemicalBook CAS DataBase List Curcumin
458-37-7

Curcumin synthesis

3synthesis methods
-

Yield:458-37-7 85%

Reaction Conditions:

Stage #1: vanillin;acetylacetonewith diboron trioxide;boric acid tributyl ester in ethyl acetate at 50; for 0.166667 h;
Stage #2: with N-butylamine in ethyl acetate at 50 - 80; for 4.25 h;

Steps:

3.2. General Method for the Synthesis of CCM (1a) and BCM (1b)

General procedure: Acetylacetone (10 mmol) was added to a solution of boric anhydride (5.0 mmol) in ethyl acetate (30 mL), followed by the addition of vanillin (20 mmol) or 4-hydroxybenzaldehyde (20 mmol) and tributyl borate (40 mmol). The reaction mixture was stirred at 50 °C for 10 min. Subsequently, n-butylamine (5.0 mmol) in ethyl acetate (5 mL) was added dropwise over 15 min at 50 °C and additionally stirred for 4 hours at 80 °C. Hydrochloric acid (1 N, 30 mL) was added, and the mixture was stirred for another 40 min. The organic layers were washed with water, dried with Na2SO4. The solvent was evaporated, and the residue was recrystallized from methanol to give the corresponding curcuminoids (1a and 1b) as yellow solids.

References:

Cao, Ya-Kun;Li, Hui-Jing;Song, Zhi-Fang;Li, Yang;Huai, Qi-Yong [Molecules,2014,vol. 19,# 10,p. 16349 - 16372]

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