Acetic Acid → HCID 14835343, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=1)=[O:9].C(O)(=O)C.OO.O>C(OO)(=O)C>[CH2:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8]2[O:9][N:1]=[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=23)=[CH:15][CH:14]=1)[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
(2-Aminophenyl) (4-ethylphenyl)methanone, 60 g, (0.27 mole) was dissolved in 700 ml of 3% peracetic acid (prepared by warming a mixture of 500 ml of glacial acetic acid and 200 ml of 30% hydrogen peroxide on a steam bath for 1/2 hr, followed by cooling to 25° C.). The solution was allowed to stand for 60 hr, then poured into two liters of water. The mixture was extracted with methylene chloride and the organic extracts were diluted with ethyl acetate and extracted with dilute sodium hydroxide. The organic phase was then concentrated and the residue was chromatographed on silica gel, eluting with benzene. The product-containing benzene fractions were concentrated and the residue was distilled. The fraction boiling at 131° C./0.02 mmHg was collected and recrystallized from isopropanol to give 33.2 g (55%) of pale yellow crystals, m.p. 42.0°-42.5° C.
Workup
- customprepared
- temperatureby warming
- extractionThe mixture was extracted with methylene chloride
- additionthe organic extracts were diluted with ethyl acetate
- extractionextracted with dilute sodium hydroxide
- concentrationThe organic phase was then concentrated
- customthe residue was chromatographed on silica gel
- washeluting with benzene
- concentrationThe product-containing benzene fractions were concentrated
- distillationthe residue was distilled
- customThe fraction boiling at 131° C./0.02 mmHg was collected
- customrecrystallized from isopropanol
Sources & evidence
- ORD record
- ord-94338af686a24353861879e586718a87
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04898874
Reaction notes
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