Toluene → Phenol, 4-[(phenylimino)methyl]-

HRID 278287Notes

Reaction equation

HRID 278287 reaction equation
[OH:1]C1C=CC=CC=1C=O.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[OH:1][C:20]1[CH:21]=[CH:22][C:17]([CH:23]=[N:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6115Aniline2×HCID 6998Salicylaldehyde

Product 1

HCID 74319Phenol, 4-[(phenylimino)methyl]-Yield 94%

Procedure

A solution of hydroxy benzaldehyde (5.00 g, 41 mmol) in toluene (200 cm3) was heated to 109° C. before aniline (1.86 g, 20 mmol) was added under nitrogen. The mixture was then allowed to cool, forming a yellow solid after 30 minutes. The reaction was continued with the further addition of aniline (1.86 g, 20 mmol). Dean and Stark apparatus was used to collect water (0.6 cm3). Reflux continued for a further 5 hours by which time 0.7 cm3 of water had collected. After cooling the mixture, a thick crystalline mass was formed which was filtered and dried under vacuum at 90° C. to give 4-hydroxybenzylidene-aniline (7.3 g, 94%) as pale cream crystals.

Workup

  1. additionwas added under nitrogen
  2. temperatureto cool
  3. customforming a yellow solid after 30 minutes
  4. customto collect water (0.6 cm3)
  5. temperatureReflux
  6. customhad collected
  7. temperatureAfter cooling the mixture
  8. customa thick crystalline mass was formed which
  9. filtrationwas filtered
  10. customdried under vacuum at 90° C.

Sources & evidence

ORD record
ord-0489a8bb32924320949f9d9d01e77ca7
Source dataset
uspto-grants-2002_03
Patent number
US06359056B1

Reaction notes

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