Ethylene Glycol → 2-(2-Hydroxyethoxy)-1-(1-naphthyl)ethanol

HRID 1198245Notes

Reaction equation

HRID 1198245 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([OH:10])[CH2:8][OH:9].[C:11]1([CH:21]2[CH2:23][O:22]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>C(OCC)(=O)C>[OH:9][CH2:8][CH2:7][O:10][CH2:23][CH:21]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[OH:22]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 64543662-(Naphthalen-1-yl)oxiraneHCID 23665647Potassium tert-butoxide

Product 1

HCID 538852792-(2-Hydroxyethoxy)-1-(1-naphthyl)ethanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4.5 g of potassium tert-butoxide and 45 ml of ethylene glycol was heated to 80° C. Thereto was dropwise added 13.7 g of 2-(1-naphthyl)oxirane in 1 hour. The resulting mixture was stirred for 1 hour at the same temperature. The reaction mixture was cooled and added to a mixture of 50 ml of ethyl acetate and 50 ml of ice water. The organic layer was separated. The aqueous layer was extracted twice each with 20 ml of ethyl acetate. The extracts were combined with the previously separated organic layer. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene/ethyl acetate=1/3) to obtain 8.3 g of 2-(2-hydroxyethoxy)-1-(1-naphthyl)ethanol.

Workup

  1. customin 1 hour
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted twice each with 20 ml of ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by column chromatography (eluant: toluene/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-4c8e8aef76cd4c069390f6480ebae298
Source dataset
uspto-grants-1994_01
Patent number
US05280032

Reaction notes

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