Potassium Carbonate → HCID 67087064, compound

HRID 2365491Notes

Reaction equation

HRID 2365491 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]1[O:21][C@H:20]1[CH2:22][OH:23]>CC(C)=O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:19][C@@H:20]([OH:21])[CH2:22][OH:23])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 6973630(-)-Glycidol2×HCID 133925134-(4-Hydroxybutyl)phenol

Product 1

HCID 67087064HCID 67087064, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 4-(4-Hydroxy-butyl)-phenol (32.7 g, 197 mmol) in acetone (600 ml) is added potassium carbonate (40.8 g, 295 mmol) followed by (S)-glycidol (13.7 ml, 207 mmol). The mixture is heated at reflux overnight. Further potassium carbonate (20 g) is added, followed by (S)-glycidol (5 g) and the mixture is heated at reflux for 72 hours. The suspension is cooled, filtered and the filtrate concentrated in vacuo. The residue is partitioned between EtOAc (500 ml) and 5% citric acid solution (500 ml). The organics are separated, dried (MgSO4) and concentrated in vacuo to give (S)-3-[4-(4-Hydroxy-butyl)-phenoxy]-propane-1,2-diol as a brown oil; 1H NMR (CDCl3): 1.56-1.74 (4H, m), 2.20 (1H, t, J=2.46 Hz), 2.61 (2H, t, J=7.6 Hz), 3.68 (2H, t, J=6.2 Hz), 3.78 (1H, dd, J=5.4 and 11.5 Hz), 3.86 (1H, dd, J=3.9 and 11.5 Hz), 4.0-4.16 (3H, m), 6.85 (2H, d, J=8.6 Hz), 7.12 (2H, d, J=8.6 Hz).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 72 hours
  5. temperatureThe suspension is cooled
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe residue is partitioned between EtOAc (500 ml) and 5% citric acid solution (500 ml)
  9. customThe organics are separated
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5a9999d12a24afb9ba6de83d1100d41
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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