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

HRID 362965Notes

Reaction equation

HRID 362965 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-34186a21514f40a1b5212375be594f47
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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