1-(2,4,5-Trihydroxyphenyl)ethanone

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CAS:1818-27-5
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CAS:1818-27-5
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CAS:1818-27-5
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CAS:1818-27-5
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1-(2,4,5-Trihydroxyphenyl)ethanone manufacturers

1-(2,4,5-Trihydroxyphenyl)ethanone Basic information
Product Name:1-(2,4,5-Trihydroxyphenyl)ethanone
Synonyms:1-(2,4,5-Trihydroxyphenyl)ethanone;acetophenone, 2,4,5-trihydroxy;Ethanone, 1-(2,4,5-trihydroxyphenyl)-;1-(2,4,5-trihydroxyphenyl)ethan-1-one
CAS:1818-27-5
MF:C8H8O4
MW:168.15
EINECS:
Product Categories:
Mol File:1818-27-5.mol
1-(2,4,5-Trihydroxyphenyl)ethanone Structure
1-(2,4,5-Trihydroxyphenyl)ethanone Chemical Properties
Melting point 200-202 °C
Boiling point 404.3±30.0 °C(Predicted)
density 1.446±0.06 g/cm3(Predicted)
storage temp. Inert atmosphere,Room Temperature
pka7.81±0.23(Predicted)
Safety Information
MSDS Information
1-(2,4,5-Trihydroxyphenyl)ethanone Usage And Synthesis
PreparationPreparation by Fries rearrangement of 1,2,4-triacetoxy-benzene,
with aluminium chloride in nitrobenzene (30–43%)
with zinc chloride at 135–140° (49–53%)
with p-toluenesulfonic acid in refluxing tetrachloroethane or benzene or without solvent at 135–140° (60%).
Synthesis
1-(6-hydroxy-1,3-benzodioxol-5-yl)Ethanone

66003-50-7

1-(2,4,5-Trihydroxyphenyl)ethanone

1818-27-5

General procedure for the synthesis of 1-(2,4,5-trihydroxyphenyl)ethan-1-one from 1-(6-hydroxybenzo[D][1,3]dioxolan-5-yl)ethan-1-one: The compound 1-(6-hydroxybenzo[D][1,3]dioxolan-5-yl)ethan-1-one (4 g, 19.03 mmol) was dissolved in chlorobenzene (20 mL) at room temperature, and in a Trichlorosilane (6.6 g, 49.47 mmol) was slowly added dropwise under nitrogen protection. The reaction mixture was heated to reflux for 24 hours. Upon completion of the reaction, the chlorobenzene was removed by rotary evaporation. The residue was dissolved in 1 M hydrochloric acid (50 mL) and extracted with ethyl acetate. The extract was post-treated and purified by silica gel column chromatography to afford 1-(2,4,5-trihydroxyphenyl)ethanone (2.1 g, 12.7 mmol) as a pale yellow solid in 66.9% yield.

References[1] Patent: CN107935982, 2018, A. Location in patent: Paragraph 0023; 0024
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 13, p. 3872 - 3875
1-(2,4,5-Trihydroxyphenyl)ethanone Preparation Products And Raw materials
Raw materials2',4',5'-TRIMETHOXYACETOPHENONE-->1-(6-hydroxy-1,3-benzodioxol-5-yl)Ethanone-->Chlorobenzene-->Trichlorosilane
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