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ChemicalBook CAS DataBase List Estragole
140-67-0

Estragole synthesis

10synthesis methods
Obtained by fractional distillation of the oil of turpentine or by treating a solution of the same oil in ether with an aqueous solution of mercuric acetate and subsequently heating the aqueous phase with zinc and sodium hydroxide; forms allyl bromide and magnesium p-methoxy phenate in ether.
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Yield:-

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium(0);potassium carbonate in tetrahydrofuran at 0 - 50;Schlenk technique;Inert atmosphere;

Steps:

Method A:
General procedure: To an oven-dried Schlenk flask, arylboronic acid (10.0 mmol), Pd(PPh3)4 (0.20 mmol), K2CO3 (10.0 mmol), THF (50 mL) are added under Ar. The mixture is then stirred at 0 oC and added with allyl bromide (10.0 mmol) by syringe slowly. Then the mixture is stirred at 50 oC for 6-12 hours as monitored by TLC. After the reaction finished, the mixture was washed by brine and extracted by ethyl ether, and purified by column chromatography on silica gel to afford the allyl benzene substrates. (eluent: hexane).

References:

Wu, Shang;Zhang, Ying;Jiang, Hongyan;Ding, Ning;Wang, Yanbin;Su, Qiong;Zhang, Hong;Wu, Lan;Yang, Quanlu [Tetrahedron Letters,2020,vol. 61,# 26,art. no. 152053] Location in patent:supporting information

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