4-Nitrobenzaldehyde → HCID 91452445, compound

HRID 853940Notes

Reaction equation

HRID 853940 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:7]=[CH:6][C:5]=1[O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[O:3].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)([O-:24])=[O:23].C(O)C.[OH-].[Na+]>C(OCC)(=O)C>[F:21][C:18]([F:19])([F:20])[CH2:17][O:16][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][C:12]([F:13])([F:14])[F:15])=[CH:9][C:4]=1[C:2](=[O:3])[CH:1]=[CH:29][C:28]1[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 702EthanolHCID 14798Sodium HydroxideHCID 27360731-(2,5-Bis(2,2,2-trifluoroethoxy)phenyl)ethan-1-one

Product 1

HCID 91452445HCID 91452445, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared by stirring a mixture of 2,5-bis(2,2,2-trifluoroethoxy)acetophenone (200 mg, 0.633 mmol), 4-nitrobenzaldehyde (96 mg, 0.633 mmol), ethanol (5 ml) and saturated NaOH (50 ul) at room temperature for 4 h. The mixture was diluted with ethyl acetate (100 ml), washed with water and saturated NaCl. The crude was dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography using hexane:ethyl acetate (4:1, 3:1) to give a yellow solid (33 mg, 12%). 1H NMR (CDCl3): 8.26 (d, J=9.0 Hz, 2H), 7.74 (d, J=9.0 Hz, 2H), 7.72 (d, J=16.2 Hz, 1H), 7.61 (d, J=15.6 Hz, 1H), 7.36 (d, J=3.0 Hz, 1H), 7.18 (dd, J=3.3, 9.0 Hz, 1H), 6.96 (d, J=9.0 Hz, 1H), 4.49-4.35 (m, 4H).

Workup

  1. washwashed with water and saturated NaCl
  2. dry with materialThe crude was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6ece3b3409714d70921a1ee4acdf6eaf
Source dataset
uspto-grants-2007_08
Patent number
US07256219B2

Reaction notes

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