Ethanol → HCID 19821136, compound

HRID 2050752Notes

Reaction equation

HRID 2050752 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-5c5d4dd6c07d478db6c0547457019ce2
Source dataset
uspto-grants-1991_05
Patent number
US05015260

Reaction notes

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