Water → [4-(Aminomethyl)phenyl]methanol

HRID 354154

Reaction equation

HRID 354154 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)#[N:8].O.[OH-].[Na+]>C(OCC)C>[NH2:8][CH2:7][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 160549p-Cyanobenzyl alcoholHCID 21226445Aluminium lithium hydride

Product 1

HCID 6496943[4-(Aminomethyl)phenyl]methanolYield 29.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of LiAlH4 (285 mg, 7.52 mmol) in diethylether (10 mL)at 0° C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t., the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0-15% MeOH in CH2Cl2) gave 152 mg (29%)of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30% MeOH in CH2Cl2+3.5% NH4OH).

Workup

  1. temperatureThe grey reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. filtrationThe resulting white slurry was filtered
  4. washwashed with CH2Cl2 (20 mL)
  5. extractionExtraction
  6. customwith additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation
  7. customyielded an oil, which upon flash chromatography (0-15% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-540c6957674f40af93e8dc47237265a5
Source dataset
uspto-grants-2004_06
Patent number
US06756393B2

Linked notes

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