Acetic Acid → 2-Methyl-4-methoxy-5-(2-hydroxypropyl)aminophenol

HRID 2050757Notes

Reaction equation

HRID 2050757 reaction equation
CO.S([O:7][C:8]1[CH:13]=[C:12]([NH:14][CH2:15][CH:16]([OH:18])[CH3:17])[C:11]([O:19][CH3:20])=[CH:10][C:9]=1[CH3:21])(=O)(=O)C.[OH-].[Na+].C(O)(=O)C>O>[CH3:21][C:9]1[CH:10]=[C:11]([O:19][CH3:20])[C:12]([NH:14][CH2:15][CH:16]([OH:18])[CH3:17])=[CH:13][C:8]=1[OH:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 198211542-Methyl-4-methoxy-5-(2-hydroxypropyl)aminophenyl mesylate

Product 1

HCID 198211342-Methyl-4-methoxy-5-(2-hydroxypropyl)aminophenolYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 100 ml of methanol was added 2.0 g (13.1 mmol) of 2-methyl-4-methoxy-5-(2-hydroxypropyl)aminophenyl mesylate. After conducting nitrogen substitution at room temperature, 40 ml of 7.5N aqueous solution of sodium hydroxide was added to the mixture and the resulting mixture was heated under reflux for 7 hours with blowing nitrogen gas thereinto. After allowing to cool, the mixture was neutralized with acetic acid and poured into 400 ml of water. The resulting solution was extracted with 400 ml of ethyl acetate. The organic layer was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain an oily matter. The oily matter was crystallized from the solvent mixture of hexane/ethyl acetate (1:1 by volume) to give 2.30 g (10.9 mmol) of 2-methyl-4-methoxy-5-(2-hydroxypropyl)aminophenol. The yield was 49%.

Workup

  1. customat room temperature
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 7 hours with blowing nitrogen gas
  4. temperatureto cool
  5. extractionThe resulting solution was extracted with 400 ml of ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customto obtain an oily matter
  10. customThe oily matter was crystallized from the solvent mixture of hexane/ethyl acetate (1:1 by volume)

Sources & evidence

ORD record
ord-d81de6fd2fb6491caec3ac71af9eab8c
Source dataset
uspto-grants-1991_05
Patent number
US05015260

Reaction notes

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