Ethylene Glycol → HCID 14988337, compound

HRID 846629Notes

Reaction equation

HRID 846629 reaction equation
[OH-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[CH2:7](Br)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O>[C:10]1(/[CH:9]=[CH:8]/[CH2:7][O:5][CH2:4][CH2:3][OH:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 98116Bromomethylstyrene

Product 1

HCID 14988337HCID 14988337, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8 Milliliters of 85% sodium hydroxide aqueous solution mixed with 46 g of ethylene glycol was heated at 40°-50° C., and 15 g of cinnamyl bromide was added dropwise thereto. After the addition was finished, the reaction mixture was heated at 100°-110° C. for 2 hours. The reaction mixture was allowed to cool, and poured into 50 ml of water then extracted with ether. The ether extract was washed with water and a saturated aqueous solution of sodium chloride in this order, and dried with anhydrous sodium sulfate. The solvent was removed by evaporation, the residue thus obtained was purified by means of a silica gel column chromatography (eluent: chloroform) to yield 5.5 g of 2-[3-phenyl- 2(E)-propenyloxy]ethanol.

Workup

  1. temperaturewas heated at 40°-50° C.
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated at 100°-110° C. for 2 hours
  4. temperatureto cool
  5. extractionthen extracted with ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride in this order, and dried with anhydrous sodium sulfate
  9. customThe solvent was removed by evaporation
  10. customthe residue thus obtained
  11. customwas purified by means of a silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-a38f4fd2037c47c08f2c54d1726da542
Source dataset
uspto-grants-1992_08
Patent number
US05137889

Reaction notes

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