Aromatic ketones containing only acetyl groups
- PDF / 329,878 Bytes
- 62 Pages / 595.276 x 841.89 pts (A4) Page_size
- 45 Downloads / 180 Views
C10H9BrO4 Syntheses
OH COCH3
Br
mol.wt. 273.08
HO COCH3
-Preparation by bromination of resodiacetophenone, *with NBS in refluxing dioxane for 10 h (97%) [55]; *with bromine, for 6 h at r.t. [1463], in cooled acetic acid [6]. -Also refer to: [669].
m.p. 205° [6], 202-203° [1463];
1H
NMR [55], IR [55], UV [55].
1,1'-(5-Bromo-2,4,6-trihydroxy-1,3-phenylene)bis-ethanone [98149-38-3]
C10H9BrO5 Synthesis
OH Br HO
mol.wt. 289.08
COCH3 OH COCH3
-Preparation by Friedel-Crafts acylation of 2-bromophloroglucinol with acetyl chloride or acetic anhydride in the presence of boron trifluoride (72-78%) [1561]. m.p. 150-152° [1561].
1,1'-(4-Chloro-6-hydroxy-1,3-phenylene)bis-ethanone [30335-99-0]
C10H9ClO3
mol.wt. 212.63
Syntheses
OH COCH3
-Obtained by Fries rearrangement, *of 4-acetyl-3-chlorophenyl acetate with aluminium chloride at 120° for 20 min (35%) [1260]; Cl *of 3-chlorophenyl acetate with aluminium chloride at COCH3 175-180° for 3 h (by-product) [1452]. -Also obtained from 5-acetyl-6-chloro-2,3-dimethylbenzofuran by oxidation with chromium trioxide in dilute acetic acid at 50° for 30 min, followed by hydrolysis of the resulting keto ester (18%) [1260]. m.p. 84° [1452], 75° [1260]; b.p.9 167° [1260];
1H
NMR [1452], MS [1452].
336
HYDROXYACETOPHENONES
1,1'-(5-Chloro-2-hydroxy-1,3-phenylene)bis-ethanone [71643-62-4]
C10H9ClO3 Syntheses
OH CH3CO
mol.wt. 212.63
COCH3
Cl
-Preparation by Fries rearrangement of 2-(acetyloxy)5-chloroacetophenone with aluminium chloride for 1 h at 130°, then 1 h at 140° (80%) [1312]. -Also refer to: [671] [984]. b.p.6 120° [1312].
1,1'-(5-Fluoro-2-hydroxy-1,3-phenylene)bis-ethanone [106823-62-5]
C10H9FO3 Synthesis
OH CH3CO
mol.wt. 196.18
COCH3
F
-Preparation by Fries rearrangement of 2-acetyl-4-fluorophenyl acetate (b.p. 124-126°) with aluminium chloride at 130-140° for 3 h (71%) [1268]. b.p. 130-135° [1268]; IR [1268].
1,1'-(4-Hydroxy-5-nitro-1,3-phenylene)bis-ethanone [100245-07-6]
C10H9NO5 Synthesis
OH NO 2
mol.wt. 223.19
COCH3
COCH3
-Preparation by nitration of 5-acetyl-2-hydroxyacetophenone at -20° using standard reagents (51%) [506]. m.p. 104-105° [506].
1,1'-(2,4-Dihydroxy-5-nitro-1,3-phenylene)bis-ethanone [103264-32-0]
C10H9NO6 Syntheses
OH CH3CO
mol.wt. 239.18
COCH3
-Preparation by reaction of 1,3-dinitroquinolizin-4-one with sodio-2,4,6-heptanetrione in DMF for 1.5 h between -15 to 10° (57%) [69]. OH -Also obtained by nitration of 2,4-diacetylresorcinol with a NO 2 nitric acid (d = 1.42)/sulfuric acid (d = 1.84) mixture in acetic acid at 0° for 1 h (41%) [41]. -Also obtained by Fries rearrangement of 4-nitroresorcinol diacetate in nitrobenzene with aluminium chloride at 95-100° for 2 h or at r.t. for 72 h (38%) [41]. m.p. 142-143° [69], 139-140° [41];
1H
NMR [69], IR [69].
AROMATIC KETONES CONTAINING ONLY ACETYL GROUPS
337
1,1'-(4,6-Dihydroxy-5-nitro-1,3-phenylene)bis-ethanone [103262-48-2]
C10H9NO6
mol.wt. 239.18
Syntheses
OH COCH3
NO 2
-Preparation by Fries rearrangement of 2-nitroresorcinol diacetate with aluminium chlori
Data Loading...
