Ethylene Glycol → 1-(4-Benzyloxyphenyl)-2-(2-hydroxyethoxy)ethanol

HRID 862507Notes

Reaction equation

HRID 862507 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[CH2:7]([OH:10])[CH2:8][OH:9].[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22](C2CO2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>CS(C)=O.C(OCC)(=O)C>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:7]([OH:10])[CH2:8][O:9][CH2:1][CH2:2][OH:4])=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 132487172-[4-(Benzyloxy)phenyl]oxiraneHCID 23665647Potassium tert-butoxide

Product 1

HCID 538391451-(4-Benzyloxyphenyl)-2-(2-hydroxyethoxy)ethanol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

9.5 g of potassium tert-butoxide was added to 92 ml of ethylene glycol. The mixture was heated to 80° C. Thereto was dropwise added, in 3 hours, a solution of 34.7 g of 2-(4-benzyloxyphenyl)oxirane dissolved in 220 mi of dimethyl sulfoxide. The resulting mixture was stirred for 30 minutes at the same temperature. The reaction mixture was cooled and added to a mixture of 1 liter of ice water and 600 ml of ethyl acetate. The resulting mixture was adjusted to pH 7 with 6N hydrochloric acid. The organic layer was separated. The aqueous layer was extracted with 200 ml of ethyl acetate. The extract was 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: chloroform/ethanol=10/1) to obtain 25 g of 1-(4-benzyloxyphenyl)-2-(2-hydroxyethoxy)ethanol.

Workup

  1. additionThereto was dropwise added, in 3 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with 200 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: chloroform/ethanol=10/1)

Sources & evidence

ORD record
ord-c5c64bad841f44c2871826b635b6ce2d
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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