Acetic Acid → HCID 22020975, compound

HRID 1354593Notes

Reaction equation

HRID 1354593 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][C:9](=O)[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl.[C:15](O)(=O)C>C(O)C.O>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:15])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 3626592HCID 3626592, compound

Product 1

HCID 22020975HCID 22020975, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the 4-chloro-2-benzooxazolinone (0.10 mol) in 200 mL ethanol is added LiOH (0.20 mol) in 100 mL of water. The solution is refluxed for 8 hr and cooled. The solution is neutralized with 1N HCl and extracted with ethyl acetate followed by drying over MgSO4. The solution is concentrated and taken up in 200 mL of toluene and 0.10 mol of acetic acid. The solution is refluxed in a Dean Stark trap for 12 hours, concentrated and purified by flash chromatography.

Workup

  1. temperatureThe solution is refluxed for 8 hr
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. dry with materialby drying over MgSO4
  5. concentrationThe solution is concentrated
  6. temperatureThe solution is refluxed in a Dean Stark trap for 12 hours
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-0663c0c1e4fe4d68ac8749998a9ed2d4
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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