Water → 3-(Benzhydrylidene-amino)-phenol

HRID 2181505Notes

Reaction equation

HRID 2181505 reaction equation
[C:1](=[NH:14])([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.N[C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.O>C1(C)C=CC=CC=1>[C:1](=[N:14][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 115683-AminophenolHCID 136809Benzophenone imine

Product 1

HCID 218772693-(Benzhydrylidene-amino)-phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(Benzhydrylidene-amino)-phenol was prepared as follows: A stirred solution of benzophenone imine (15.0 g, 82.8 mmol) and 3-aminophenol (9.03 g, 82.8 mmol) in 25 mL toluene was heated at reflux with removal of H2O with a Dean-Stark trap for 3.5 h. The crystals that formed from the cooled reaction mixture were collected by vacuum filtration, washed with hexanes and air dried. In this manner, 3-(benzhydrylidene-amino)-phenol was obtained as a light yellow solid (17.3 g, 76%): 1H NMR (CDCl3) δ7.64 (d, 2H, J=7.1 Hz), 7.38 (d, 1H, J=7.1 Hz), 7.34-7.15 (m, 7H), 7.04 (d, 2H, J=7.2 Hz), 6.88 (t, 1H, J=8.1 Hz), 6.82 (d, 1H, J=8.2 Hz), 6.23 (s, 1H), 6.21 (d, 1H, J=7.8 Hz). Anal. Calc. for C19H15NO: C, 83.49; H, 5.53; N, 5.12. Found: C, 83.51; H, 5.65; N, 5.03.

Workup

  1. custom3-(Benzhydrylidene-amino)-phenol was prepared
  2. customThe crystals that formed from the cooled reaction mixture
  3. filtrationwere collected by vacuum filtration
  4. washwashed with hexanes and air
  5. customdried

Sources & evidence

ORD record
ord-a971dd669d04407c8b296a9a51b63f8b
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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