Styrene Oxide → HCID 22714722, compound

HRID 351914Notes

Reaction equation

HRID 351914 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([S:8]([OH:11])(=[O:10])=[O:9])[CH:7]=1.[Na].[OH-].[Na+].[CH2:16]1[O:24][CH:17]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][OH:24])=[C:6]([S:8]([OH:11])(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 7276Styrene OxideHCID 14798Sodium HydroxideHCID 5172275-chloro-2-hydroxybenzenesulfonic acidHCID 5360545Sodium

Product 1

HCID 22714722HCID 22714722, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-hydroxybenzenesulfonic acid, sodium salt (7.9 g), NaOH (1.37 g) and water (25 ml) was heated on a boiling water bath until the mixture became homogeneous. Styreneoxide (2.4 g) was added dropwise over a period of 10 minutes and the mixture was heated with stirring on a boiling water bath for 1 hr. It was extracted with ether and the aqueous solution was evaporated to dryness. The residue was treated with water and the insoluble white precipitate was collected by filtration and washed with 5 mL water to obtain 2-(4-chloro-2-sulfophenoxy)-2-phenylethanol (4.1 g).

Workup

  1. temperaturewas heated on a boiling water bath until the mixture
  2. temperaturethe mixture was heated
  3. extractionIt was extracted with ether
  4. customthe aqueous solution was evaporated to dryness
  5. additionThe residue was treated with water
  6. filtrationthe insoluble white precipitate was collected by filtration
  7. washwashed with 5 mL water

Sources & evidence

ORD record
ord-88b78f7afb8d45b7aaafed2253c9474d
Source dataset
uspto-grants-2004_06
Patent number
US06743820B2

Reaction notes

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