Acetone → HCID 67087064, compound

HRID 2281565Notes

Reaction equation

HRID 2281565 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-:14].[K+].[K+].[CH3:19][C:20]([CH3:22])=[O:21]>>[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:14])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium Carbonate2×HCID 133925134-(4-Hydroxybutyl)phenol

Product 1

HCID 67087064HCID 67087064, compound

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)-glycidolgg (13.7 ml, 207 mmol). The mixture is heated at reflux overnight. Further potassium carbonate (20 g) is added, followed by (S)-glycidolgg (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-1c8d4467161e4a97bb41a99bd5328007
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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