Water → Ethanol, 2-(ethylphenylamino)-, 1-acetate

HRID 276743Notes

Reaction equation

HRID 276743 reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21].O>CC(C)=O>[C:20]([O:12][CH2:11][CH2:10][N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 623382-(N-ethylanilino)ethanol

Product 1

HCID 113382Ethanol, 2-(ethylphenylamino)-, 1-acetateYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

51.8 g of 2-(N-ethylanilino)ethanol and 31.7 g of triethylamine were dissolved in 300 ml of acetone. To this was added slowly 25 g of acetyl chloride while cooling the resulting reaction solution with ice water. The resulting solution was then stirred for 6 hours at room temperature for reaction. 200 ml of water was then poured into the solution. The organic layer was extracted with ethyl acetate and dried with sodium sulfate. The solvent was then distilled off under reduced pressure to obtain 64.9 g of 2-(N-ethylanilino)ethyl acetate.

Workup

  1. temperaturewhile cooling
  2. extractionThe organic layer was extracted with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-bd2e94ce3b8043488d2dd31264c76a54
Source dataset
uspto-grants-2002_03
Patent number
US06355396B1

Reaction notes

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