Benzaldehyde, 4-(diphenylamino)- → (4-(Diphenylamino)phenyl)methanol

HRID 1814722Notes

Reaction equation

HRID 1814722 reaction equation
[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C.[OH-].[Na+]>[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 4311764Sodium borohydride

Product 1

HCID 11323339(4-(Diphenylamino)phenyl)methanolYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The compound (1) obtained in Example 1-1, that is, 4-(diphenylamino)benzaldehyde, (4.2 g) was dissolved in 50 mL of ethanol and a solution prepared by dissolving 0.29 g of NaBH4 in 0.1 M aqueous solution of NaOH (15 mL) was slowly added thereto. The reactant solution was reacted at room temperature for 4 hours. An organic layer was separated from the reactant solution using methylene chloride and recrystallized in a methylene chloride/hexane solvent, yielding 92% of a white solid. Data of NMR spectra confirmed that the product had the same structure as the compound (2) in the reaction scheme 2.

Workup

  1. customa solution prepared
  2. additionwas slowly added
  3. customThe reactant solution was reacted at room temperature for 4 hours
  4. customAn organic layer was separated from the reactant solution
  5. customrecrystallized in a methylene chloride/hexane solvent

Sources & evidence

ORD record
ord-0546ba01bb7942039b91eeaf8d2accaa
Source dataset
uspto-grants-2005_04
Patent number
US06878468B2

Reaction notes

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