p-Aminoacetophenone → 4-Amino-alpha-methylbenzenemethanol

HRID 450038Notes

Reaction equation

HRID 450038 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].[BH4-].[Na+]>CO>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH:2]([OH:3])[CH3:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7468p-AminoacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 857534-Amino-alpha-methylbenzenemethanolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-amino acetophenone (0.5 g, 3.7 mmol) in methanol (10 ml), was added sodium borohydride (0.27 g, 7.4 mmol, 2 eq) at 0° C. The reaction mixture was stirred for 3 hr at room temperature. The solvent was evaporated and water was added. The compound was extracted with ethyl acetate, then the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to yield pure 1-(4-amino-phenyl)-ethanol (0.4 g, 80%).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionThe compound was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cb06a862c1374d518862cadc08beb88f
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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