Water → 4-[4-(Aminomethyl)phenyl]phenol

HRID 493470Notes

Reaction equation

HRID 493470 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[K+]>C1COCC1>[NH2:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 1406104'-Hydroxy-4-biphenylcarbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 162278894-[4-(Aminomethyl)phenyl]phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4′-Hydroxy-biphenyl-4-carbonitrile (10.00 g, 51.2 mmol) in 150 mL of anhydrous THF was added under nitrogen dropwise over 30 minutes to a suspension of LAH (2.91 g, 76.7 mmol) in 200 mL of anhydrous THF at room temperature. After the addition the reaction was refluxed for 20 h (overnight). In the following order 2.91 mL of water, 2.91 mL of 15% KOH and 8.73 mL of water were added dropwise. The reaction was stirred for 30 minutes at room temperature. The solid was removed by filtration and dried under reduced pressure to give a yellow solid which was used in the next step without additional purification.

Workup

  1. additionAfter the addition the reaction
  2. temperaturewas refluxed for 20 h (overnight)
  3. customThe solid was removed by filtration
  4. customdried under reduced pressure
  5. customto give a yellow solid which
  6. customwas used in the next step without additional purification

Sources & evidence

ORD record
ord-64c0b4c6376a40d98a50ab2ae3eb2a7e
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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