Methanol → HCID 85336771, compound

HRID 853933Notes

Reaction equation

HRID 853933 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].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.CO.[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:27][C:26]1[CH:29]=[CH:30][C:23]([Cl:22])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 27360731-(2,5-Bis(2,2,2-trifluoroethoxy)phenyl)ethan-1-one

Product 1

HCID 85336771HCID 85336771, 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-chlorobenzaldehyde (89 mg, 0.633 mmol), methanol (5 ml) and saturated NaOH (200 ul) at room temperature for 4 h. The mixture was diluted with ethyl acetate (100 ml), wash with water (50 ml) and saturated aqueous NaCl (50 ml), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using hexane:ethyl acetate (5:1, 4:1) to give a yellow solid (143 mg, 51%). 1H NMR (CDCl3): 7.65 (d, J=15.9 Hz, 1H), 7.54 (d, J=8.4 Hz, 2H), 7.44 (d, J=15.9 Hz, 1H), 7.38 (d, J=8.4 Hz, 2H), 7.31 (d, J=3.3 Hz, 1H), 7.14 (dd, J=3.3, 9.3 Hz, 1H), 6.95 (d, J=9.0 Hz, 1H), 4.45-4.32 (m, 4H).

Workup

  1. washwash with water (50 ml) and saturated aqueous NaCl (50 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4b6ce353e0984653aafda733e5ab5da8
Source dataset
uspto-grants-2007_08
Patent number
US07256219B2

Reaction notes

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