2'-Aminoacetophenone → 2-Amino-alpha-methylbenzenemethanol

HRID 1647470Notes

Reaction equation

HRID 1647470 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH3:11]>CO>[OH:12][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:3])[CH3:11]

Participants

4

Reactant 2

HCID 110862'-AminoacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 1120582-Amino-alpha-methylbenzenemethanolYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (40 g, 1.0 mol) was added portionwise to a stirred solution of o-aminoacetophenone (80 g) in methanol (800 ml) at 0°, allowing the effervescence to subside between each addition. Cooling was removed and the mixture allowed to warm to reflux temperature to complete the reaction. When cool, the solvent was evaporated and the residue partioned between dichloromethane-water. The organic solution was washed successively with water and brine, dried (anhyd. MgSO4), filtered and evaporated to a light yellow oil which crystallised from petroleum spirit (40°-60°) to give white crystals (52 g, 64%), m.p. 50°-52°.

Workup

  1. additionto subside between each addition
  2. temperatureCooling
  3. customwas removed
  4. temperatureto warm
  5. temperatureto reflux temperature
  6. customthe reaction
  7. temperatureWhen cool
  8. customthe solvent was evaporated
  9. washThe organic solution was washed successively with water and brine
  10. dry with materialdried (anhyd. MgSO4)
  11. filtrationfiltered
  12. customevaporated to a light yellow oil which
  13. customcrystallised from petroleum spirit (40°-60°)

Sources & evidence

ORD record
ord-f5ccd551038046dd9bfdc9f74992e48d
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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