Allylbenzene → 2-(Phenylmethyl)oxirane

HRID 982101Notes

Reaction equation

HRID 982101 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:13]=[CH2:14]>C(Cl)Cl.CCOCC>[CH2:12]([CH:13]1[O:9][CH2:14]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 9309AllylbenzeneHCID 70297m-Chloroperbenzoic acid2×

Product 1

HCID 948262-(Phenylmethyl)oxiraneYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (mCPBA; 17 g, 0.1 mol) in 120 mL of methylene chloride was added (at ambient temperature) dropwise to a solution of allyl benzene (10 g, 85 mmol) in 200 mL of methylene chloride. After the reaction mixture was stirred for 5 h with a mechanical stirrer, 5 additional grams of m-CPBA were added and the reaction mixture stirred for another 2 h. The reaction mixture was then diluted with 200 mL of ether, washed with 2×100 mL of aqueous sodium bisulfite solution, 100 mL of aqueous sodium bicarbonate solution and 100 mL of brine. The organic solution was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by bulb-to-bulb distillation (60° C., 0.1 mm) to give 8.5 g (77% yield) of 1-benzyl ethylene oxide as a clear colorless liquid.

Workup

  1. stirringthe reaction mixture stirred for another 2 h
  2. washwashed with 2×100 mL of aqueous sodium bisulfite solution, 100 mL of aqueous sodium bicarbonate solution and 100 mL of brine
  3. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was purified by bulb-to-bulb distillation (60° C., 0.1 mm)

Sources & evidence

ORD record
ord-68f213df0b9d4601acfa211a8029acbd
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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