Methanol → 1-[2,5-Bis(2,2,2-trifluoroethoxy)phenyl]-3-(4-methylphenyl)-2-propen-1-one

HRID 853928Notes

Reaction equation

HRID 853928 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].[C:22]1([CH3:30])[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=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:30][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 77254-MethylbenzaldehydeHCID 14798Sodium HydroxideHCID 27360731-(2,5-Bis(2,2,2-trifluoroethoxy)phenyl)ethan-1-one

Product 1

HCID 907298881-[2,5-Bis(2,2,2-trifluoroethoxy)phenyl]-3-(4-methylphenyl)-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared by heating a mixture of 2,5-bis(2,2,2-trifluoroethoxy)acetophenone (200 mg, 0.633 mmol), p-tolualdehyde (75 ul, 0.633 mmol), methanol (5 ml) and NaOH (200 ul, 10M) for 24 h. The mixture was cooled to room temperature, diluted with ethyl acetate (100 ml), wash with water and saturated aqueous NaCl, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography using hexane:ethyl acetate (4:1) to give a yellow solid (32 mg, 12.2%). 1H NMR (CDCl3): 7.67 (d, J=15.6 Hz, 1H), 7.50 (d, J=8.4 Hz, 2H), 7.40 (d, J=15.6 Hz, 1H), 7.28 (d, J=3.3 Hz, 1H), 7.22 (d, J=8.1 Hz, 2H), 7.12 (dd, J=3.3, 9.3 Hz, 1H), 6.96 (d, J=8.7 Hz, 1H), 4.44-4.33 (m, 4H), 2.39 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-90207729a5b2405e8a0e912ea96eef0c
Source dataset
uspto-grants-2007_08
Patent number
US07256219B2

Reaction notes

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