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

HRID 2268268Notes

Reaction equation

HRID 2268268 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-604156f45b054e5eb4212c40f3cdc15e
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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