Acetic Acid → [3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanone

HRID 390263Notes

Reaction equation

HRID 390263 reaction equation
[CH3:1][O:2][CH:3]([O:28][CH3:29])[C:4]1[CH:5]=[C:6]([C:13](N2CCOCC2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)C#N)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].CC(O)=[O:32]>>[CH3:1][O:2][CH:3]([O:28][CH3:29])[C:4]1[CH:5]=[C:6]([C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:32])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 58625101(3-Dimethoxymethyl-4-nitro-phenyl)-morpholin-4-yl-phenyl-acetonitrile

Product 1

HCID 19816024[3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanone

Procedure

(3-Dimethoxymethyl-4-nitro-phenyl)-morpholin-4-yl-phenyl-acetonitrile (0.7 mol) in CH3CO2H (1500 ml) was stirred and refluxed for 30 min. The mixture was poured on ice/water and extracted with diisopropyl ether. The organic layer was washed with alkalic water and water. The organic layer was dried (MgSO4) and evaporated to yield a residue. The aqueous layers which contained product were extracted with CH2Cl2. The organic layer was dried (MgSO4) and evaporated to yield a residue. The combined residues were purified on a glass filter over silica gel (eluent: CH2Cl2). The pure fractions were collected and evaporated to yield the title compound as a residue.

Workup

  1. temperaturerefluxed for 30 min
  2. additionThe mixture was poured on ice/water
  3. extractionextracted with diisopropyl ether
  4. washThe organic layer was washed with alkalic water and water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customto yield a residue
  8. extractionwere extracted with CH2Cl2
  9. dry with materialThe organic layer was dried (MgSO4)
  10. customevaporated
  11. customto yield a residue
  12. customThe combined residues were purified on a glass
  13. filtrationfilter over silica gel (eluent: CH2Cl2)
  14. customThe pure fractions were collected
  15. customevaporated

Sources & evidence

ORD record
ord-13ff663476364d7892fc8dcf8c098530
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

Loading…