1-(2-Hydroxy-3,4,5-trimethoxyphenyl)ethanone synthesis

12synthesis methods

Product Name:1-(2-Hydroxy-3,4,5-trimethoxyphenyl)ethanone
CAS Number:30225-96-8
Molecular formula:C11H14O5
Molecular Weight:226.23

Preparation by reaction of dimethyl sulfate on 2,5-di-hydroxy-3,4-dimethoxyacetophenone with potassium carbonate in refluxing benzene (73%).

30225-80-0
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1-(2-Hydroxy-3,4,5-trimethoxyphenyl)ethanone

30225-96-8
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Yield:30225-96-8 690.1 mg

Reaction Conditions:

with boron trifluoride diethyl etherate at 100; for 0.5 h;Inert atmosphere;

Steps:

1-(2-Hydroxy-3,4,5-trimethoxyphenyl)ethanone (4)

To the crude 2,3,4-trimethoxyphenylacetate (1.2 g),BF3·OEt2 (4 mL, 31.8 mmol) was added at room temperatureunder Ar gas. After stirring for 30 min at 100 °C, thereaction mixture was poured into H2O, and the resultingmixture was extracted with EtOAc. The organic layer waswashed with saturated NaHCO3 aqueous solution, brine,and then dried over Na2SO4. Removal of the solvent gave a residue, which was purified by column chromatographyusing hexane-EtOAc (8:2, v/v) as the eluent to give 1-(2-hydroxy-3,4,5-trimethoxyphenyl)ethanone (4) (690.1 mg,68%) as a yellow solid. 1H-NMR (CDCl3; 400 MHz) δ12.44 (1H, s), 6.93 (1H, s), 4.04 (3H, s), 3.92 (3H, s), 3.86(3H, s), 2.59 (3H, s); 13C-NMR (CDCl3; 100 MHz) δ 203.1,153.1, 149.9, 145.0, 141.4, 114.2, 107.4, 61.3, 61.0, 59.7,26.7.

References:

Ishikawa, Kazuki;Takahashi, Kazunori;Hosoi, Syun;Takeda, Hisashi;Yoshida, Hinaka;Wakana, Daigo;Tsubuki, Masayoshi;Sato, Fumihiko;Tojo, Motoaki;Hosoe, Tomoo [Journal of Antibiotics,2019,vol. 72,# 2,p. 71 - 78]