Water → 2,3-Epoxy-1-[4-(2-ethoxycarbonylethyl)-phenoxy]-propane

HRID 1417120Notes

Reaction equation

HRID 1417120 reaction equation
[H-].[Na+].C(OC(=O)[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH3:8])C.[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl.[OH2:22]>CN(C)C=O>[O:21]1[CH2:20][CH:19]1[CH2:17][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:7][CH2:8][C:20]([O:21][CH2:19][CH3:17])=[O:22])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 12785115Ethyl 2-(4-hydroxyphenyl)propanoate

Product 1

HCID 113796982,3-Epoxy-1-[4-(2-ethoxycarbonylethyl)-phenoxy]-propane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.56 g (148.5 mmol) of sodium hydride is added to 24.03 g (123.74 mmol) of 2-(4-hydroxyphenyl)-propanoic acid ethyl ester in 400 ml of dimethylformamide and stirred for 1 hour at room temperature (under nitrogen). 34.35 g (371.22 mmol) of epichlorohydrin is added and then heated for 24 hours at 70° C. It is cooled in an ice bath to 0° C. and 800 ml of water is carefully added. Then, it is extracted twice with 350 ml of ether each. The combined ether phases are washed once with 300 ml of water, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel (mobile solvent: hexane/ethyl acetate=20:1)

Workup

  1. temperatureheated for 24 hours at 70° C
  2. temperatureIt is cooled in an ice bath to 0° C.
  3. extractionThen, it is extracted twice with 350 ml of ether each
  4. washThe combined ether phases are washed once with 300 ml of water
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue is chromatographed on silica gel (mobile solvent: hexane/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-91dfb448dd9d4a1abea0832e38ce11a1
Source dataset
uspto-grants-1999_03
Patent number
US05876698

Reaction notes

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