Sodium Hydroxide → (4-(Diphenylamino)phenyl)methanol

HRID 1786788

Reaction equation

HRID 1786788 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+].[OH-].[Na+]>CO.O>[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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 4311764Sodium borohydride

Product 1

HCID 11323339(4-(Diphenylamino)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2B (3.637 g, 13.3 mmol) in methanol was added dropwise at 0° C. a solution of NaBH4 added to 3.9 g NaOH dissolved in 7.8 mL H2O. The solution was allowed to stir at room temperature overnight. Water was added and the product was extracted with ether (2×) and washed with brine (2×). The combined ether extracts were dried over MgSO4. The solvent was removed and the product was purified using flash chromatography with a hexanes and then ethyl acetate. The ethyl acetate fraction was collected and the solvent removed to reveal 2.667 g (74%) of a honey yellow crystal solid. 1H NMR (CDCl3): δ4.63 (d, 2H), δ6.97-7.06 (m, 6H), δ7.09 (m, 2H), δ7.20-7.28 (m, 6H); m/z 298.1 (M++Na), 276.1 (M++H), 258.1 (M+-H2O).

Workup

  1. extractionthe product was extracted with ether (2×)
  2. washwashed with brine (2×)
  3. dry with materialThe combined ether extracts were dried over MgSO4
  4. customThe solvent was removed
  5. customthe product was purified
  6. customThe ethyl acetate fraction was collected
  7. customthe solvent removed

Sources & evidence

ORD record
ord-d21e6c91ab2540298a5395a1d73bf922
Source dataset
uspto-grants-2009_03
Patent number
US07507840B2

Linked notes

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