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ChemicalBook CAS DataBase List Protocatechuic acid
99-50-3

Protocatechuic acid synthesis

12synthesis methods
-

Yield:99-50-3 100%

Reaction Conditions:

with aluminium(III) iodide;diisopropyl-carbodiimide in acetonitrile at 80; for 18 h;

Steps:

Hydroxychavicol (4-Allylbenzene-1,2-diol, 2); General Procedure

General procedure: To a suspension of AlI3 (5.5 mmol, 1.1 equiv) in hot CH3CN (40 mL) were added sequentially DIC (0.379 g, 3 mmol, 0.6 equiv) and eugenol (1, 0.821 g, 5.0 mmol). The mixture was stirred for 18 h at 80 °C, and then it was cooled to r.t., acidified with HCl (2 mol/L, 10 mL), and extracted with EtOAc (3 × 50 mL). The organic phases were combined, washed with sat. aq Na2S2O3 (10 mL) and brine (10 mL), and was dried (MgSO4). The solvent was removed on a rotary evaporator and the residue was purified by flash column chromatography (PE/EtOAc, 4:1) to afford 2 (0.750 g, 99%) as a white solid

References:

Sang, Dayong;Wang, Jiahui;Zheng, Yun;He, Jianyuan;Yuan, Caili;An, Qing;Tian, Juan [Synthesis,2017,vol. 49,# 12,p. 2721 - 2726]

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