Acetic Acid → 4-(4-Chlorophenyl)-2,3-dihydro-1,3-oxazol-2-one

HRID 47927

Reaction equation

HRID 47927 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[O-:12][C:13]#[N:14].[K+].[CH:16](O)([CH3:18])[CH3:17].C(O)(=O)C>O>[CH:16]([O:11][CH:8]([CH3:5])[CH3:9])([CH3:18])[CH3:17].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:14][C:13](=[O:12])[O:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 5870851-(4-Chlorophenyl)-2-hydroxyethan-1-oneHCID 11378442Potassium cyanate

Product 2

HCID 7914Diisopropyl EtherHCID 114241254-(4-Chlorophenyl)-2,3-dihydro-1,3-oxazol-2-oneYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4′-chloro-2-hydroxyacetophenone (3.41 g), potassium cyanate (3.25 g) and isopropanol (15 mL) was added dropwise acetic acid (2.88 g) at 50° C. The obtained mixture was stirred at 50° C. for 5 h and water (34 mL) was added. The precipitated crystals were collected by filtration, and washed with water and then with isopropyl ether to give 4-(4-chlorophenyl)-2-oxo-4-oxazoline (3.33 g; yield 85.1%).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-0c97421450554779ba21a39d6fa20d87
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Linked notes

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