Acetic Acid → Diacetamate

HRID 1381630Notes

Reaction equation

HRID 1381630 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].[C:16](O)(=[O:18])[CH3:17]>>[CH3:10][C:9]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]([CH3:17])=[O:18])=[CH:4][CH:3]=1)=[O:11]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4034-AminophenolHCID 7918Acetic Anhydride

Product 1

HCID 17499Diacetamate

Conditions

Temperature
20 °C

Procedure

A 500 mL, 3-neck flask fitted with mechanical stirrer, an inert gas inlet topped reflux condenser, and a thermocouple was charged with acetic acid (32 mL) and 4-aminophenol (10.9 g, 0.10 mol). Acetic anhydride (30.2 g, 0.30 mol) was added in one portion and the brown, clear solution was heated to 100°-110° C. and maintained at that temperature for 16 hours. Heating was stopped and the reaction mixture was allowed to cool slowly with stirring (under argon). After approximately 1 hour the mixture had cooled to 20° C. and precipitation began. The mixture was cooled to ~0° C. (ice-salt bath) and maintained at that temperature for 6 hours and was then filtered. The pale-pink solid was dried in vacuum to yield 16.1 g, 0.08 mol of 4-acetoxyacetanilide (mp 140°-142° C.). The molecular structure was confirmed by IR and 1H NMR analyses.

Workup

  1. customA 500 mL, 3-neck flask fitted with mechanical stirrer, an inert gas inlet
  2. temperaturetopped reflux condenser
  3. temperaturethe brown, clear solution was heated to 100°-110° C.
  4. temperaturemaintained at that temperature for 16 hours
  5. temperatureHeating
  6. temperatureto cool slowly
  7. customprecipitation
  8. temperatureThe mixture was cooled to ~0° C. (ice-salt bath)
  9. temperaturemaintained at that temperature for 6 hours
  10. filtrationwas then filtered
  11. customThe pale-pink solid was dried in vacuum

Sources & evidence

ORD record
ord-871837df69f5472caa126f71464c5006
Source dataset
uspto-grants-1989_02
Patent number
US04803254

Reaction notes

Loading…