Sodium Hydroxide → Styrene Oxide

HRID 2180325Notes

Reaction equation

HRID 2180325 reaction equation
Cl[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[OH-].[Na+]>ClCCl>[CH2:2]1[O:4][CH:3]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 928982-Chloro-1-phenylethanol

Product 1

HCID 7276Styrene OxideYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (+)-2-chloro-1-phenylethanol (156.6 mg, 1.0 mmol, 97.5% ee) in dichloromethane (2.0 ml) and a 2.0 M aqueous solution of sodium hydroxide (1.0 ml, 2.0 mmol) were mixed and stirred at room temperature for 4 hours. To the solution was added dichloromethane (2.0 ml), and the dichloromethane layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation. The residue was purified by silica gel column chromatography to give a desired compound, (+)-styrene oxide (115.2 mg; yield: 95.9%; optical purity: 97.5% ee).

Workup

  1. washthe dichloromethane layer was washed with a saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed by evaporation
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e3ee3da41834b6889e0c204c707fd13
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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