Acetic Acid → HCID 22020975, compound

HRID 1793689Notes

Reaction equation

HRID 1793689 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-30ebfc903be741bf9bf3bdcb75840f8a
Source dataset
uspto-grants-2006_07
Patent number
US07081454B2

Reaction notes

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