Sodium Hydroxide → [4-(Aminomethyl)phenyl]methanol

HRID 400217Notes

Reaction equation

HRID 400217 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.O.[OH-].[Na+]>C1COCC1.O>[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 655264-(Aminomethyl)Benzoic AcidHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 6496943[4-(Aminomethyl)phenyl]methanolYield 38.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A! 4-(Aminomethyl)benzoic acid (20 g, 0.132 mole) was added to a suspension of lithium aluminium hydride (5.5 g, 0,145 moles) in 300 ml of THF, at room temperature. The suspension was refluxed for 4 hours, the cooled to room temperature and added with, successively, a mixture THF/water 7:1 (32 ml), 32% sodium hydroxide (10 ml) and water (40 ml). The formed solid was filtered off and the solvent evaporated under vacuum to provide 7 g of 4-(aminomethyl)benzyl alcohol che was directly used in the next step.

Workup

  1. temperatureThe suspension was refluxed for 4 hours
  2. filtrationThe formed solid was filtered off
  3. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-ae771e1a25344d29a48a161ce5ddfaab
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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