Compounds derived from acetic acid
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C 8H 4F4O 2 Synthesis
OH F
mol.wt. 208.11
COCH3
-Obtained by hydrolytic cleavage of 2-amino-3-(2-hydroxy3,4,5,6-tetrafluorobenzoyl)acrylic acid (I) or of 3-(2-hydroxy-3,4,5,6-tetrafluorobenzoylmethylene)F F piperazin-2-one (II) in boiling aqueous sodium hydroxide F for 20 min (53% and 44% yields, respectively) [179]. m.p. 36° [179]; 1H NMR [179], 19F NMR [179], IR [179]. 1-(2,3,5,6-Tetrafluoro-4-hydroxyphenyl)ethanone [145797-51-9]
C 8H 4F4O 2
mol.wt. 208.11
Synthesis
OH F
F
F
F COCH3
-Preparation by reaction of acetyl chloride on 2,3,5,6-tetrafluorophenol with aluminium chloride in carbon disulfide at 5° (10%) [720]. m.p. 109-111° [720].
1-(3,5-Dibromo-2-hydroxy-4-nitrophenyl)ethanone C8H5Br2NO4 Synthesis
OH Br
mol.wt. 338.94
COCH3
NO2 Br
-Preparation by reaction of bromine on 2-hydroxy-4-nitroacetophenone in refluxing acetic acid-sodium acetate mixture (68%) [1649]. m.p. 157° [1649].
1-(2,4,6-Tribromo-3-hydroxyphenyl)ethanone [49605-14-3]
C8H5Br3O2 Synthesis
OH Br
Br COCH3 Br
mol.wt. 372.84
-Preparation by bromination of 3-hydroxyacetophenone in water at 50° (94%) [521] [650]. m.p. 127°5 [521] [650].
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HYDROXYACETOPHENONES
1-(3,4,5-Tribromo-2-hydroxyphenyl)ethanone [145666-19-9]
C8H5Br3O2 Synthesis not yet described.
OH Br
mol.wt. 372.84
COCH3
-Refer to: [1205] (compound 1h).
Br Br 1-(4-Chloro-2-hydroxy-3,5-dinitrophenyl)ethanone C8H5ClN2O6 Syntheses
OH COCH3
NO2
mol.wt. 260.59
-Preparation by nitration of 4-chloro-2-hydroxyacetophenone (77%) [924]. -Also obtained (by-product) by nitration of 2-acetyl5-chlorophenyl acetate in sulfuric acid solution at -10° (24%) [924].
Cl NO2 m.p. 149-150° [924].
1-(4,6-Dichloro-2-hydroxy-3-nitrophenyl)ethanone [81515-01-7]
C8H5Cl2NO4 Synthesis
OH NO2
COCH3
Cl
mol.wt. 250.04
-Preparation by nitration of 2,4-dichloro-6-hydroxyacetophenone with potassium nitrate in concentrated sulfuric acid, first between -10° and 0°, then at r.t. [1483].
Cl
m.p. 62-64° [1483]. 1-(3,4,6-Trichloro-2-hydroxyphenyl)ethanone [126712-08-1]
C8H5Cl3O2
mol.wt. 239.48
Synthesis
OH Cl
COCH3
Cl
Cl
m.p. 103-104° [1778];
-Preparation by Fries rearrangement of 2,3,5-trichlorophenyl acetate with aluminium chloride without solvent at 130-140° (49%) [1778]. 1H
NMR [1778], MS [1778].
COMPOUNDS DERIVED FROM ACETIC ACID
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1-(Trichloro-4-hydroxyphenyl)ethanone [94650-96-1]
C8H5Cl3O2
OH Cl
Synthesis not yet described.
OH Cl
Cl
or Cl Cl COCH3
mol.wt. 239.48
Cl COCH3
-Identified in wheat and rye straw pulp bleaching and combined mill effluents [617]. -Identified during control of effluent from the manufacturing of bleached pulp and paper from sugarcane bagasse [616].
1-(2,3,6-Trichloro-4,5-dihydroxyphenyl)ethanone [154638-87-6]
C8H5Cl3O3
mol.wt. 255.48
Synthesis
OH HO
Cl
Cl
Cl COCH3
-Obtained (by-product) by chlorination of 4-hydroxy3-methoxyacetophenone in dioxane-water mixture at 40° (4%) [1456]. MS [1456].
1-(2,4,5-Trichloro-3,6-dihydroxyphenyl)ethanone [7714-14-9]
C8H5Cl3O3 Syntheses
OH Cl
mol.wt. 255.48
Cl
-Preparation by reaction
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