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

HRID 378641

Reaction equation

HRID 378641 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-74f7b1681da446ec8ea0f484ba7dcf7f
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Linked notes

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