ChemicalBook CAS DataBase List 1-(2-Hydroxy-4-iodo-phenyl)-ethanone

1-(2-Hydroxy-4-iodo-phenyl)-ethanone synthesis

5synthesis methods

Product Name:1-(2-Hydroxy-4-iodo-phenyl)-ethanone
CAS Number:39730-66-0
Molecular formula:C8H7IO2
Molecular Weight:262.04

Preparation by Fries rearrangement of 3-iodophenyl acetate with aluminium chloride
in chlorobenzene, at 125–135° (64%)
in nitrobenzene, at 110–140° (40–45%).

42861-71-2 Synthesis

42861-71-2
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$29.00/250mg

39730-66-0
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$535.00/1g

Yield:39730-66-0 88%

Reaction Conditions:

with boron trifluoride diacetate at 180; for 12 h;Fries Phenol Ester Rearrangement;

Steps:

1-(2-Hydroxy-4-iodophenyl)ethanone (22)

3-Iodophenyl acetate 21 (250 mg, 0.95 mmol) was dissolved in boron trifluoride aceticacid complex (4 mL). The mixture was stirred at 180 °C for 12 h. The reaction medium wasallowed to cool and then was diluted in dichloromethane (20 mL). Then, 5M Sodium hydroxideaqueous solution was added (20 mL). The aqueous layer was extracted with dichloromethane(100 mL) and washed with distilled water (100 mL). The aqueous layerswere acidified with 5M hydrochloric acid solution (20 mL) and extracted with dichloromethane.The combined organic layers were dried over sodium sulfate and filtered. Thesolvent was evaporated in vacuo and the residue was purified by silica gel column chromatographyusing cyclohexane/ethyl acetate (8/2) as the eluent to give compound 22 (219mg, 88% yield) as a beige powder. Rf 0.68 (cyHex/AcOEt 8:2); Mp: 52-53 °C (lit. 51.5-52 °C) [59]; 1H NMR (400 MHz, CDCl3) δ 12.18 (s, 1H, OH), 7.50-7.24 (m, 2H), 7.27-7.07 (m,1H), 2.53 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3) δ 204.1 (C=O), 162.2 (C2), 131.2 (C5),128.3 (C6), 127.8 (C3), 119.0 (C1), 103.7 (C4), 26.5 (CH3); IR (cm-1): 1620, 1600, 1543, 1475,1365, 1317, 1284, 1211; MS (ESI) m/z (%): 263.0 (100) [M + H]+; UPLC purity = 100%, tR 2.68min. Literature spectroscopic data [59].

References:

Bach, Stéphane;Baratte, Blandine;Bazin, Marc-Antoine;Brachet-Botineau, Marie;Dao, Viet Hung;Denevault-Sabourin, Caroline;Gouilleux, Fabrice;Logé, Cédric;Marchand, Pascal;McCarthy, Florence O.;Ourliac-Garnier, Isabelle;Robert, Thomas;Thiéfaine, Jér?me;da Silva, Teresinha Gon?alves [Molecules,2021,vol. 26,# 21,art. no. 6572]