Acetic Anhydride → N-(2-Acetoxyethyl)-N-methylaniline

HRID 1086383Notes

Reaction equation

HRID 1086383 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:1][CH2:2][CH2:3][N:4]([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 623402-(N-Methylanilino)ethanol

Product 1

HCID 12570555N-(2-Acetoxyethyl)-N-methylaniline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 74.0 g (0.489 mol) of N-(2-hydroxyethyl)-N-methylaniline in 100 mL of pyridine was treated dropwise with 55 g (0.54 mol) of acetic anhydride. The resulting mixture was heated at reflux for 10 hr, then cooled and poured onto 500 g of ice. The mixture was extracted three times with dichloromethane (3×100 mL), the combined extracts were dried using magnesium sulfate (MgSO4) and the solvent was evaporated. The residue was distilled at reduced pressure, producing 84.2 g of a slightly yellow oil, b.p. 107°-116° C. (0.4 mm).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 10 hr
  3. temperaturecooled
  4. extractionThe mixture was extracted three times with dichloromethane (3×100 mL)
  5. customthe combined extracts were dried
  6. customthe solvent was evaporated
  7. distillationThe residue was distilled at reduced pressure
  8. customproducing 84.2 g of a slightly yellow oil, b.p. 107°-116° C. (0.4 mm)

Sources & evidence

ORD record
ord-03b0e541bbd24cc3bd424de33a9fe5b9
Source dataset
uspto-grants-1991_07
Patent number
US05029979

Reaction notes

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