Styrene → 1-Phenyl-1,2-ethanediol

HRID 2083884Notes

Reaction equation

HRID 2083884 reaction equation
C=C[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[N+]1([O-])[CH2:15][CH2:14][O:13]CC1.O.CC(C)=[O:20].C(#N)C>>[C:3]1([CH:14]([OH:13])[CH2:15][OH:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 7501StyreneHCID 82029Methyl morpholine oxideHCID 18799168Acetonitrile acetone water

Product 1

HCID 71491-Phenyl-1,2-ethanediolYield 86.2%

Procedure

To 9 mL of a solvent consisting of water-acetone-acetonitrile (1:1:1) were added 1 g of styrene, 1.5 g of N-methylmorpholine-N-oxide and 1.24 g of the metal oxide carried on the cross-linked polymer compound which was obtained in Example 2, followed by allowing a reaction to take place at room temperature for 5 hours with stirring. After the reaction, the metal oxide carried on the cross-linked polymer compound was recovered by filtration from the reaction solution, and the reaction solution was extracted with ethyl acetate and the organic layer was washed with water, concentrated and purified by column chromatography to give 1.2 g of 1-phenyl-1,2-ethanediol (yield: 86.2%).

Workup

  1. customwas obtained in Example 2
  2. customa reaction
  3. customat room temperature
  4. customfor 5 hours
  5. customAfter the reaction
  6. filtrationwas recovered by filtration from the reaction solution
  7. extractionthe reaction solution was extracted with ethyl acetate
  8. washthe organic layer was washed with water
  9. concentrationconcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-6594b70b33cb4ad6b281b26f55f8e7ed
Source dataset
uspto-grants-2004_04
Patent number
US06716792B2

Reaction notes

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