Phenol → N-(1,1-dimethyl-2-phenoxyethyl)acetamide

HRID 1956878Notes

Reaction equation

HRID 1956878 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=1>C(OCC)(=O)C>[CH3:11][C:12]([NH:13][C:9](=[O:10])[CH3:8])([CH3:15])[CH2:14][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 744964,5-Dihydro-2,4,4-trimethyloxazole

Product 1

HCID 18349669N-(1,1-dimethyl-2-phenoxyethyl)acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of phenol (33.2 g) and 2,4,4-trimethyloxazoline (18.1 g) was heated in a stirred pressure vessel at 220° C. for 48 hours. The oil obtained on cooling was dissolved in ethyl acetate, washed with 5M sodium hydroxide solution, water, brine, then dried and evaporated to give an oil which was distilled under high vacuum to give N-(1,1-dimethyl-2-phenoxyethyl)acetamide, b.p. 115°-122° C. at 0.67 mbar.

Workup

  1. customThe oil obtained
  2. temperatureon cooling
  3. washwashed with 5M sodium hydroxide solution, water, brine
  4. customdried
  5. customevaporated
  6. customto give an oil which
  7. distillationwas distilled under high vacuum

Sources & evidence

ORD record
ord-591ebd4134d24135a4e2325cd9418b18
Source dataset
uspto-grants-1998_07
Patent number
US05780642

Reaction notes

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