Allylbenzene → 2-(Phenylmethyl)oxirane

HRID 1089022Notes

Reaction equation

HRID 1089022 reaction equation
ClC1C(C(OO)=[O:9])=CC=CC=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 125873982-Chlorobenzene-1-carboperoxoic acid

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 qrams 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, 1×100 mL of aqueous sodium bicarbonate solution and 1×100 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. addition5 additional qrams of m CPBA were added
  2. stirringthe reaction mixture stirred for another 2 h
  3. washwashed with 2×100 mL of aqueous sodium bisulfite solution, 1×100 mL of aqueous sodium bicarbonate solution and 1×100 mL of brine
  4. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was purified by bulb-to-bulb distillation (60° C., 0.1 mm)

Sources & evidence

ORD record
ord-7e7332bb8be04e9ca3650916cbbb47ca
Source dataset
uspto-grants-1990_10
Patent number
US04963568

Reaction notes

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