Acetic Acid → 2-Amino-alpha-methylbenzenemethanol

HRID 1377700Notes

Reaction equation

HRID 1377700 reaction equation
[BH4-].[Na+].[C:3]([OH:6])(=O)[CH3:4].[H][H].[NH2:9][CH2:10][C:11]([C:13]1C=CC=[CH:15][CH:14]=1)=O.[C:19](=O)(O)[O-].[Na+]>C1COCC1.O>[CH3:19][CH:3]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:11][C:10]=1[NH2:9])[OH:6]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 11952PhenacylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 1120582-Amino-alpha-methylbenzenemethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (1.12 g, 29.6 mmol) was stirred under nitrogen in THF (40 mL) in an ice bath. Acetic acid (3.38 mL, 3.55 g, 59.2 mmol) was added dropwise. The mixture was stirred until hydrogen evolution had ceased, then neat 2-aminoacetophenone (2.0 g, 14.8 mmol) was added dropwise. The mixture was stirred at ambient temperature for 5 days, then treated with water (40 mL) and neutralized with saturated aqueous sodium bicarbonate. The mixture was extracted with ether, and the combined ether layers were dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give methyl-2-aminophenyl carbinol.

Workup

  1. extractionThe mixture was extracted with ether
  2. dry with materialthe combined ether layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-25076d9a69154d22a7ef30bd70593386
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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