tert-Butyl hydroperoxide → HCID 57305581, compound

HRID 1604056Notes

Reaction equation

HRID 1604056 reaction equation
[O:1]=[CH:2]/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9].CC([O:19]O)(C)C.[OH-].[Na+].CCOCC.O>CO>[CH:2]([C@@H:3]1[O:19][C@H:4]1[C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:1]

Participants

6

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 14798Sodium HydroxideHCID 13370780HCID 13370780, compoundHCID 21584184Diethylether water

Product 1

HCID 57305581HCID 57305581, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
35 °C

Procedure

Methyl 3-(3-oxo-1E-propenyl)benzoate (0.67 g, 3.52 mmol) and 10 ml of methanol was added dropwise to 0.58 ml of 70% 1,1-dimethylethylhydroperoxide (4.2 mmol) in 5 ml of methanol. The pH was maintained at pH 8.0-8.5 throughout with 1N sodium hydroxide. The mixture was stirred at about 35° C. for 1.5 hrs. The reaction mixture was poured into ether/water and the ether layer was washed 3× with water and 1× with brine, dried over sodium sulfate, and concentrated. Flash chromatography using 10:1 followed by 2:1 hexane/ethyl acetate provided the product, methyl trans-3-(3-formyloxiranyl)benzoate as the pure trans epoxide.

Workup

  1. washthe ether layer was washed 3× with water and 1× with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6d6ebed91f91437c878fe9a2fca50764
Source dataset
uspto-grants-1999_11
Patent number
US05990326

Reaction notes

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