m-Chloroperbenzoic acid → HCID 59568660, compound

HRID 1186939Notes

Reaction equation

HRID 1186939 reaction equation
[CH:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:6]2[C:7](=[O:10])[O:8][CH2:9][C:5]=2[C:4]=1[CH3:14])=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH3:14][C:4]1[C:5]2[CH2:9][O:8][C:7](=[O:10])[C:6]=2[CH:11]=[C:12]([CH3:13])[C:3]=1[CH:1]1[CH2:2][O:23]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68431569HCID 68431569, compound

Product 1

HCID 59568660HCID 59568660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Ethenyl-4,6-dimethyl-2-benzofuran-1(3H)-one (150 mg, 0.797 mmol), mCPBA (275 mg, 1.59 mmol), were combined together in DCM (20 mL) and stirred at room temperature for 12 h. The reaction mixture was then diluted with DCM and washed with Na2S2O3 solution, NaHCO3 solution, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness. The resulting residue was then re-dissolved DCM, absorbed onto silica gel, concentrated, and loaded into silica column for separation giving 4,6-dimethyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one.

Workup

  1. washwashed with Na2S2O3 solution, NaHCO3 solution, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customre-dissolved DCM, absorbed onto silica gel
  6. concentrationconcentrated
  7. customloaded into silica column for separation

Sources & evidence

ORD record
ord-db171efab7ae44d9a5510cc6b73a6787
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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