Acetic Acid → 2(3H)-Oxazolone, 5-methyl-4-phenyl-

HRID 732177Notes

Reaction equation

HRID 732177 reaction equation
[OH:1][CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[O-:12][C:13]#[N:14].[K+].C(O)(=O)C.O>CC(O)C>[CH3:11][C:2]1[O:1][C:13](=[O:12])[NH:14][C:3]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1011212-Hydroxy-1-phenyl-1-propanoneHCID 11378442Potassium cyanate

Product 1

HCID 123070002(3H)-Oxazolone, 5-methyl-4-phenyl-Yield 37%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-hydroxy-1-phenylpropan-1-one (1.00 g, 6.66 mmol) and potassium cyanate (1.08 g, 13.3 mmol) in 2-propanol (15 mL) was added dropwise acetic acid (960 mg, 16.0 mmol) at 50° C. over 1 hr. The mixture was stirred at 50° C. for 5 hr, and the reaction mixture was poured into water. The resulting precipitate was collected by filtration and recrystallized from isopropyl ether-hexane to give the title compound (430 mg, yield 37%) as white crystals.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customrecrystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-08e3f055bd204f83bf5b32aa3b8a6221
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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