Aromatic ketones containing at least one acetyl group and one other acyl group
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C15H11NO6 HO
COCH3
mol.wt. 301.26
Synthesis -Obtained by heating 3-benzoyl-2,4-dihydroxyacetophenone-4-β-D-glucopyranoside with dilute nitric acid for 3 min (44%) [1232].
CO HO
NO 2
N.B.: A sesquihydrate was obtained by crystallisation of the ketone in water [1232]. The melting point is determined after water elimination (100°/0.04 mm/1h). m.p. 114-118° [1232]. 1-(3-Benzoyl-4-hydroxyphenyl)ethanone [13043-37-3]
C15H12O3
mol.wt. 240.26
Synthesis
HO
-Refer to: [968] [1055].
CO COCH3
1-(4-Benzoyl-3-hydroxyphenyl)ethanone [39954-75-1]
C15H12O3
mol.wt. 240.26
Synthesis
HO
-Obtained by alkaline hydrolysis of 3-(benzoyloxy)4-benzoylacetophenone (SM) (m.p. 88°) with sodium hydroxide in boiling ethanol for 15 min. SM was prepared by oxidation of 6-acetyl-2,3-diphenylbenzofuran (m.p. 119°) with chromium trioxide in acetic acid at 70-75° for 2 h [87]. CO
COCH3
m.p. 103° [87]; IR [87]. 1-(5-Benzoyl-2-hydroxyphenyl)ethanone [2589-80-2]
C15H12O3 COCH3
CO
OH
mol.wt. 240.26
Syntheses -Obtained by Fries rearrangement of 4-(acetyloxy)benzophenone with aluminium chloride (3.3 mol) at 150-160° for 1 h [178].
398
HYDROXYACETOPHENONES
-Also obtained by hydrolysis of 3-acetyl-4-(acetyloxy)-benzophenone [543]. -Also refer to: [968]. m.p. 102-103° [178], 95-96° [543];
1H
NMR [543], IR [543], MS [543].
1-(3-Benzoyl-2,4,6-trihydroxyphenyl)ethanone [31188-65-5]
C15H12O5
mol.wt. 272.26
Syntheses
OH CO
COCH3
HO
OH
-Preparation by C-acetylation of 2-benzoylphloroglucinol with boron trifluoride-acetic acid complex (76%) [1109]. -Also refer to: [968] [1423]. m.p. 145-146° [1109].
1-(4-Benzoyl-3-hydroxy-2-methylphenyl)ethanone [51846-39-0]
C16H14O3 HO
CO
CH3 COCH3
mol.wt. 254.29
Synthesis -Obtained by alkaline hydrolysis of 4-benzoyl-3-benzoyloxy-2-methylacetophenone (m.p. 102°) [1529]. m.p. 39° [1529]; IR [1529].
1-(4-Benzoyl-5-hydroxy-2-methylphenyl)ethanone [39954-81-9]
C16H14O3 Synthesis
HO COCH3
CO
mol.wt. 254.29
CH3
-Obtained by alkaline hydrolysis of 3-(benzoyloxy)4-benzoyl-6-methylacetophenone (m.p. 135°) (SM) with sodium hydroxide in boiling ethanol for 15 min. SM was obtained by oxidation of 6-acetyl-5-methyl-2,3-diphenylbenzofuran (m.p. 133°) with chromium trioxide in acetic acid at 70-75° for 2 h [87].
m.p. 92° [87]; IR [87]. 1-(5-Benzoyl-4-hydroxy-2-methylphenyl)ethanone [51846-51-6]
C16H14O3 Synthesis
HO CO
mol.wt. 254.29
CH3 COCH3
-Obtained by alkaline hydrolysis of 5-benzoyl-4-benzoyloxy-2-methylacetophenone [1529]. m.p. 108-112° [1529]; IR [1529].
AROMATIC KETONES CONTAINING AT LEAST ONE ACETYL GROUP AND ONE OTHER ACYL GROUP 1-(3-Benzoyl-2-hydroxy-4,6-dimethylphenyl)ethanone [84312-32-3]
C17H16O3 HO
mol.wt. 268.31
Synthesis
COCH 3
-Obtained by UV light irradiation of 2-acetyl-3,5-dimethylphenyl benzoate in benzene for 10 h (13%) [545].
CH3
CO
399
CH3 m.p. 138-139° [545];
1H
NMR [545], IR [545], UV [545], MS [545].
1-(3-Benzoyl-6-hydroxy-2,4-dimethylphenyl)ethanone [84312-33-4]
C17H16O3 CH3
COCH3 OH
CO CH3
mol.wt. 268.31
Synthesis -Obtained by UV light irr
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