ChemicalBook CAS DataBase List 5-[(1E)-2-(4-Chlorophenyl)ethenyl]-1,3-benzenediol

5-[(1E)-2-(4-Chlorophenyl)ethenyl]-1,3-benzenediol synthesis

4synthesis methods

Product Name:5-[(1E)-2-(4-Chlorophenyl)ethenyl]-1,3-benzenediol
CAS Number:823804-63-3
Molecular formula:C14H11ClO2
Molecular Weight:246.69

1-[2-(4-Chloro-phenyl)-vinyl]-3,5-diMethoxy-benzene

1032508-03-4
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5-[(1E)-2-(4-Chlorophenyl)ethenyl]-1,3-benzenediol

823804-63-3
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Yield:823804-63-3 64%

Reaction Conditions:

with boron tribromide in dichloromethane at -10 - 20; for 24 h;Inert atmosphere;

Steps:

2. General procedure for demethylation of stilbene 4

General procedure: In 6 mL of anhydrous methylene chloride, 200 mg of methoxy-stilbene 4 (0.74 mmol) was dissolved and cooled to -10 °C under argon. BBr₃ (0.6 mL, 6.3 mmol, 17% in dichloromethane) in anhydrous methylene chloride (5 mL) was added slowly, and the mixture was allowed to reach to room temperature for 3-24 h. Water was added to destroy the excess BBr₃, and the mixture was extracted twice with ethyl acetate. The organic extracts were washed with water and brine and dried, and the solvent evaporated. The crude product was purified by column chromatography on silica gel (20% EtOAc in hexane) yielding resveratrol and derivatives 1.

References:

Uzura, Saori;Sekine-Suzuki, Emiko;Nakanishi, Ikuo;Sonoda, Motohiro;Tanimori, Shinji [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 16,p. 3886 - 3891] Location in patent:supporting information

1073-67-2 Synthesis