Acetic Anhydride → N-Ethyl-N-(4-hydroxyphenyl)acetamide

HRID 463536Notes

Reaction equation

HRID 463536 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].[C:11](OC(=O)C)(=[O:13])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>CN(C=O)C>[CH2:1]([N:3]([C:11](=[O:13])[CH3:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 121194-(Ethylamino)phenolHCID 14798Sodium Hydroxide

Product 1

HCID 13457835N-Ethyl-N-(4-hydroxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Two g of p-ethylaminophenol (0.0146 moles) were dissolved in 50 ml DMF. To this was added 2.98 g of acetic anhydride (0.0292 moles). The mixture was heated at 60° for three hours and then poured over crushed ice. Sodium carbonate was added until a pH of approximately 10 was achieved. The solution and precipitated oil were extracted with chloroform, dried over anhydrous magnesium sulfate, and then evaporated to dryness leaving a residual oil. To this oil was added 5% sodium hydroxide, and the mixture was heated at 60° for one hour. The solution was cooled and then extracted with chloroform. The remaining aqueous phase was acidified with dilute HCl to achieve a pH of approximately 4, and then extracted with chloroform. The liquid was dried over anhydrous magnesium sulfate, and then evaporated to dryness. The residual brown solid material was recrystallized from an ethanol-water mixture to yield N-ethyl-4'-hydroxyacetanilide (melting point 183°-185° C.).

Workup

  1. temperatureThe mixture was heated at 60° for three hours
  2. additionpoured
  3. customover crushed ice
  4. customThe solution and precipitated oil
  5. extractionwere extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customleaving a residual oil
  9. temperaturethe mixture was heated at 60° for one hour
  10. temperatureThe solution was cooled
  11. extractionextracted with chloroform
  12. extractionextracted with chloroform
  13. dry with materialThe liquid was dried over anhydrous magnesium sulfate
  14. customevaporated to dryness
  15. customThe residual brown solid material was recrystallized from an ethanol-water mixture

Sources & evidence

ORD record
ord-19200adee2d547ed9b9d566e24d54b48
Source dataset
uspto-grants-1985_05
Patent number
US04520134

Reaction notes

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