Potassium Carbonate → HCID 66917027, compound

HRID 1183032Notes

Reaction equation

HRID 1183032 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]1[O:20][C@H:19]1[CH2:21][OH:22]>CC(C)=O>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:18][C@@H:19]([OH:20])[CH2:21][OH:22])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 824523-(4-Hydroxyphenyl)propanolHCID 6973630(-)-Glycidol

Product 1

HCID 66917027HCID 66917027, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 3-(4-hydroxyphenyl)-1-propanol (10.0 g, 66.0 mmol) and potassium carbonate (13.5 g, 100 mmol) in acetone (200 mL) is added (S)-glycidol (6.5 mL, 100 mmol). The mixture is heated at reflux for 18 h. After cooling to RT the solvent is removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer is further extracted twice with EtOAc and the combined organic portions are washed with water, brine, then dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2, EtOAc:iso-hexane, 1:1) to afford the title compound as a white solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 18 h
  3. customis removed in vacuo
  4. customthe residue partitioned between EtOAc and water
  5. extractionThe aqueous layer is further extracted twice with EtOAc
  6. washthe combined organic portions are washed with water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue is purified by flash chromatography (SiO2, EtOAc:iso-hexane, 1:1)

Sources & evidence

ORD record
ord-428c31bd176d41fc93fc5b8e527625b2
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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