Hydrogen Peroxide → HCID 14835354, compound

HRID 1198987Notes

Reaction equation

HRID 1198987 reaction equation
OO.[NH2:3][C:4]1[CH:9]=[C:8]([CH2:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>C(O)(=O)C>[CH2:10]([C:8]1[CH:7]=[CH:6][C:5]2=[C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:13][N:3]=[C:4]2[CH:9]=1)[CH3:11]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 14835353HCID 14835353, compound

Product 1

HCID 14835354HCID 14835354, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 300 ml of 30% hydrogen peroxide in 700 ml of glacial acetic acid was heated on a steam bath for 1 hr. To the cooled solution was added a solution of 64.0 g (0.284 mole) of (2-amino-4-ethylphenyl)phenylmethanone in 150 ml of glacial acetic acid. The dark reaction mixture was heated at 50°-70° C. for 0.5 hr, poured into 3 liters of ice water and let stand at ambient temperature overnight. The reaction mixture was extracted with six 200 ml portions of carbon tetrachloride. The combined carbon tetrachloride extracts were washed with three 200 ml portions of water and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to 200 ml, treated with charcoal and filtered. The filtrate was evaporated under reduced pressure to give a dark oil as residue. A 9.0 g sample was purified by chromatography (3.5×60 cm glass column; 175 g of silica gel; benzene). Fractions containing the title compound were combined and the solvent evaporated under reduced pressure to give 6.2 g (57%) of oil. The oil was dissolved in 2-propanol and cooled to dry ice acetone temperatures to give light yellow crystals, m.p. 41°-43° C.

Workup

  1. customThe dark reaction mixture
  2. temperaturewas heated at 50°-70° C. for 0.5 hr
  3. extractionThe reaction mixture was extracted with six 200 ml portions of carbon tetrachloride
  4. washThe combined carbon tetrachloride extracts were washed with three 200 ml portions of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure to 200 ml
  7. additiontreated with charcoal
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure
  10. customto give a dark oil as residue
  11. customA 9.0 g sample was purified by chromatography (3.5×60 cm glass column; 175 g of silica gel; benzene)
  12. additionFractions containing the title compound
  13. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-0413607ca1ad437d80c88805956a7c6e
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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