Benzaldehyde → Styrene Oxide

HRID 1941466Notes

Reaction equation

HRID 1941466 reaction equation
[CH2:1]([Zn]CC)C.S1CCCC1.[CH:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCCl.ClCCl>[CH2:1]1[O:18][CH:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 1127TetrahydrothiopheneHCID 178418750HCID 178418750, compound

Product 1

HCID 7276Styrene OxideYield 92%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl zinc (1.8 ml of 1.1M solution in toluene, 2.0 mmol) in 1,2-dichloroethane (6 ml) was added chloroiododomethane (218 μl. 3 mmol) at -15° C. and the reaction mixture was stirred for 15 minutes. Tetrahydrothiophene (240 μl , 3 mmol) and benzaldehyde (1 mmol) were added and the reaction mixture was warmed to room temperature. After stirring at that temperature for 1 hour the reaction mixture was refluxed for one hour. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (20 ml) and washed with saturated solution of NH4Cl (3×5 ml). The organic layer was dried over MgSO4. After filtration of the drying agent the solvent was removed in vacuo and the residue was chromatographed over silica (eluant petrol:dichloromethane (40:60) to give the title compound as a clear oil (92%).

Workup

  1. stirringAfter stirring at that temperature for 1 hour the reaction mixture
  2. temperaturewas refluxed for one hour
  3. temperatureAfter cooling to room temperature
  4. washwashed with saturated solution of NH4Cl (3×5 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationAfter filtration of the drying agent the solvent
  7. customwas removed in vacuo
  8. customthe residue was chromatographed over silica (eluant petrol:dichloromethane (40:60)

Sources & evidence

ORD record
ord-24cd117a316a4bc3bbce8cd0d9df7a9a
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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