Potassium Carbonate → [2-(Propan-2-ylamino)phenyl]methanol

HRID 1290890Notes

Reaction equation

HRID 1290890 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].O.O.O.[C:15]([O-])(=O)[CH3:16].[Na+].[C:20](=O)([O-])[O-].[K+].[K+]>[OH-].[Na+].CC(C)=O.C(O)C.O.C(O)(=O)C>[CH:15]([NH:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([CH3:16])[CH3:20]

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 214392-Aminobenzyl alcoholHCID 4311764Sodium borohydrideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 10797123[2-(Propan-2-ylamino)phenyl]methanol

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

While maintaining at 0° to 5° C., a solution of 140 g of sodium borohydride in 500 ml of 0.5% sodium hydroxide aqueous solution was dropwise added over 2 hours to a solution mixture of 150 g of 2-aminobenzyl alcohol, 300 g of sodium acetate trihydrate, 850 ml of acetic acid, 950 ml of water, 275 ml of ethanol and 500 ml of acetone. Stirring was continued at the same temperature for an hour. Thereafter the reaction mixture was neutralized with potassium carbonate, followed by extraction with hexane. The organic layer was washed with water and then with saturated sodium chloride aqueous solution. The solvent was distilled off under vacuum. Distillation under vacuum gave 142 g of 2-isopropylaminobenzyl alcohol.

Workup

  1. temperatureWhile maintaining at 0° to 5° C.
  2. waitwas continued at the same temperature for an hour
  3. extractionfollowed by extraction with hexane
  4. washThe organic layer was washed with water
  5. distillationThe solvent was distilled off under vacuum
  6. distillationDistillation under vacuum

Sources & evidence

ORD record
ord-be38540b97994ba899b987a90c36eea7
Source dataset
uspto-grants-1998_05
Patent number
US05753673

Reaction notes

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