Water → Phenol, 5-[(2-hydroxyethyl)amino]-4-methoxy-2-methyl-

HRID 1029997Notes

Reaction equation

HRID 1029997 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[CH:7][C:6]=1[N:13]1[CH2:17][CH2:16][O:15]C1=O.O>C(O)(=O)C>[CH3:11][C:9]1[CH:10]=[C:5]([O:4][CH3:3])[C:6]([NH:13][CH2:17][CH2:16][OH:15])=[CH:7][C:8]=1[OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19821132HCID 19821132, compound

Product 1

HCID 9794190Phenol, 5-[(2-hydroxyethyl)amino]-4-methoxy-2-methyl-Yield 45.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

10 ml of 5N sodium hydroxide was heated to 70° C., and 2.76 g (12.4 mmol) of N-(2-methoxy-4-methyl-5-hydroxyphenyl)-1,3-oxazolidin-2-one was added thereto, and then the resulting mixture was stirred at 70° C. for 1 hour. After allowing to cool, 40 ml of water was poured into the reaction mixture, and acetic acid was added thereto until no further crystals were precipitated. The crystals were filtered, washed with water and recrystallized from the solvent mixture of water/ethanol (4:1, by volume). Thus, 1.10 g (5.6 mmol) of 2-methyl-4-methoxy-5-(β-hydroxyethylamino)phenol was obtained. The yield was 45%.

Workup

  1. temperatureto cool
  2. additionwas added
  3. customuntil no further crystals were precipitated
  4. filtrationThe crystals were filtered
  5. washwashed with water
  6. customrecrystallized from the solvent mixture of water/ethanol (4:1, by volume)

Sources & evidence

ORD record
ord-a04b393520c14199922277890d2a3cfc
Source dataset
uspto-grants-1992_04
Patent number
US05104414

Reaction notes

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