Phenol → N-(2-phenoxyethyl)propionamide

HRID 1982585Notes

Reaction equation

HRID 1982585 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([C:10]1[O:11][CH2:12][CH2:13][N:14]=1)[CH3:9]>O>[O:7]([CH2:12][CH2:13][NH:14][C:10](=[O:11])[CH2:8][CH3:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 664122-Ethyl-2-oxazoline

Product 1

HCID 13508823N-(2-phenoxyethyl)propionamideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenol (13.1 moles) was heated to 150° and stirred under N2 as 2-ethyl-2-oxazoline (12.2 moles) was added over 1 hr. The mixture was heated to 175±3°. After heating 16 hr the oil was cooled to about 140°, and then it was poured into water (12 L) with vigorous stirring. The mixture was stirred and cooled, and at about 25° the mixture was seeded with crystalline amide product. The material solidified and the supernatant was decanted. The residual solid was stirred with 17 L of hot (85°) water. The mixture was cooled to 25°, seeded with the amide product, and the mixture refrigerated. The resulting granular solid was collected on a filter, rinsed with several portions of water and left to air dry. This gave a 92% yield of material, m.p. 61.5°-64°.

Workup

  1. additionwas added over 1 hr
  2. temperatureThe mixture was heated to 175±3°
  3. temperatureAfter heating 16 hr the oil
  4. temperaturewas cooled to about 140°
  5. temperaturecooled
  6. customat about 25°
  7. customthe supernatant was decanted
  8. stirringThe residual solid was stirred with 17 L of hot (85°) water
  9. temperatureThe mixture was cooled to 25°
  10. customThe resulting granular solid was collected on a filter
  11. washrinsed with several portions of water
  12. waitleft to air
  13. customdry

Sources & evidence

ORD record
ord-8094d3eeebbf427ca46fcc80d5b60a21
Source dataset
uspto-grants-1986_06
Patent number
US04596884

Reaction notes

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