Potassium Carbonate → HCID 66917027, compound

HRID 2281597Notes

Reaction equation

HRID 2281597 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 g, 66 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 hours. After cooling to room temperature 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, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography on silica eluting with 1:1 EtOAc/iso-hexane to afford (S)-3-[4-(3-Hydroxy-propyl)-phenoxy]-propane-1,2-diol as a white solid; 1H NMR (CDCl3): 1.20 (1H, br), 1.85 (2H, pent, J=6.8 Hz), 1.98 (1H, br), 2.58 (1H, br), 2.65 (2H, tr, J=6.9 Hz), 3.56 (2H, tr, J=6.8 Hz), 3.72 (1H, m), 3.83 (1H, m), 4.00 (2H, dd, J=2.1 Hz, J=6.5 Hz), 4.09 (1H, br), 6.82 (2H, d, J=7.4 Hz), 7.10 (2H, d, J=7.4 Hz).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 18 hours
  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 column chromatography on silica eluting with 1:1 EtOAc/iso-hexane

Sources & evidence

ORD record
ord-700f3ad9af2d44dab10ca4ee540d7d53
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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