Water → Benzaldehyde, 4-[bis(4-formylphenyl)amino]-2-hydroxy-

HRID 1183789Notes

Reaction equation

HRID 1183789 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=2)[C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([O:18]C)[CH:11]=2)=[CH:5][CH:4]=1)=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].O>ClCCl>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:20]2[CH:21]=[CH:22][C:23]([CH:26]=[O:27])=[CH:24][CH:25]=2)[C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([OH:18])[CH:11]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 24814179HCID 24814179, compound

Product 1

HCID 24814389Benzaldehyde, 4-[bis(4-formylphenyl)amino]-2-hydroxy-Yield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of compound 9 (310 mg, 860 μmol) in dichloromethane (5 mL) is added dropwise to a suspension of aluminium chloride (AlCl3, 575 mg, 4.31 mmol, 5 eq.) in dichloromethane (10 mL) at −10° C. The mixture is stirred under reflux for 24 hours. It is then poured into a mixture of water and ice, and it is then vigorously stirred for 10 minutes. It is extracted with dichloromethane. The organic phase is washed with water and with brine, dried and concentrated to give a solid which is triturated in hexane to give 260 mg (754 μmol) of compound 10 in the form of a yellow powder (yield: 87%).

Workup

  1. temperatureunder reflux for 24 hours
  2. stirringis then vigorously stirred for 10 minutes
  3. extractionIt is extracted with dichloromethane
  4. washThe organic phase is washed with water and with brine
  5. customdried
  6. concentrationconcentrated
  7. customto give a solid which
  8. customis triturated in hexane

Sources & evidence

ORD record
ord-5cf810faa211411ea3f453499f337ca4
Source dataset
uspto-grants-2014_03
Patent number
US08664400B2

Reaction notes

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