Potassium Carbonate → 3-[3-(Benzhydrylidene-amino)phenoxy]-cyclohex-2-enone

HRID 1861058Notes

Reaction equation

HRID 1861058 reaction equation
[C:1](=[N:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1](=[N:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][C:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5683453-Chlorocyclohex-2-en-1-oneHCID 218772693-(Benzhydrylidene-amino)-phenol

Product 1

HCID 218772453-[3-(Benzhydrylidene-amino)phenoxy]-cyclohex-2-enone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of the 3-(benzhydrylidene-amino)-phenol (10.47 g, 38.3 mmol), 3-chloro-cyclohex-2-enone (5.00 g, 38.3 mmol) and potassium carbonate (5.82,42.1 mmol) in 150 mL of acetone was heated at reflux overnight. The cooled reaction mixture was filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting hexanes/EtOAc (2:1). In this manner, 3-[3-(benzhydrylidene-amino)-phenoxy]-cyclohex-2-enone was obtained as a yellow solid, (8.82 g, 63%): 1H NMR (CDCl3) δ 7.78 (d, 2H, J=7.0 Hz), 7.50 (d, 1H, J=7.1 Hz), 7.45 (d, 2H, J=7.7 Hz), 7.34-7.10 (m, 6H), 6.69 (d, 1H, J=8.0 Hz), 6.61 (d, 1H, J=8.0 Hz), 6.38 (s, 1H), 4.89 (s, 1H), 2.55 (t, 2H, J=6.2 Hz), 2.34 (t, 2H, J=6.2 Hz), 2.06 (m, 2H). Anal. Calc. for C25H21NO2.0.2H2O: C, 80.92; H, 5.81; N, 3.78. Found: C, 81.12; H, 5.81; N, 3.72.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluting hexanes/EtOAc (2:1)

Sources & evidence

ORD record
ord-fb66c224b0bf49b1adf3303a91386442
Source dataset
uspto-grants-2003_03
Patent number
US06531491B1

Reaction notes

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