Ethanol → HCID 19821136, compound

HRID 1029995Notes

Reaction equation

HRID 1029995 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:12]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[C:10]([O:17][CH3:18])=[CH:9][C:8]=1[CH3:19])(=O)C.C(O)C>C(O)(=O)C>[CH3:19][C:8]1[CH:9]=[C:10]([O:17][CH3:18])[C:11]([NH:13][C:14](=[O:16])[CH3:15])=[CH:12][C:7]=1[OH:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 19821145HCID 19821145, compound

Product 1

HCID 19821136HCID 19821136, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 35 ml of a 0.4N aqueous solution of sodium hydroxide were added 1.70 g (7.17 mmol) of 2-methyl-4-methoxy-5-acetylaminophenyl acetate and 10 ml of ethanol. The mixture was stirred at room temperature for 10 minutes. When crystals were completely dissolved, the stirring was ceased. Then 0.3 ml of acetic acid was added and thus crystals were precipitated. The crystals were collected by filtration, purified by column chromatography (Silica Gel 60, trade name, manufactured by Merck Co., 230-400 mesh, 200 g, eluent: ethyl acetate) and recrystallized from the solvent mixture of ethyl acetate/hexane (2:1). Thus 1.05 g (5.38 mmol) of 2-methyl-4-methoxy-5-acetylaminophenol was obtained. The yield was 75%.

Workup

  1. dissolutionWhen crystals were completely dissolved
  2. customthus crystals were precipitated
  3. filtrationThe crystals were collected by filtration
  4. custompurified by column chromatography (Silica Gel 60, trade name, manufactured by Merck Co., 230-400 mesh, 200 g, eluent: ethyl acetate)
  5. customrecrystallized from the solvent mixture of ethyl acetate/hexane (2:1)

Sources & evidence

ORD record
ord-cce48bc9446443a29a1337f064ab5680
Source dataset
uspto-grants-1992_04
Patent number
US05104414

Reaction notes

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