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