Benzyl Chloride → (S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid

HRID 459192Notes

Reaction equation

HRID 459192 reaction equation
[OH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCO>[CH2:20]([O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@H:2]([OH:1])[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 9920545Latifolicinin C acid

Product 1

HCID 11818113(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-Hydroxy-3-(4-hydroxy-phenyl)-propionic acid (121 g, 0.664 mol) (Wang et al. Tetrahedron Lett. 1998, 39, 5501) in absolute EtOH (2 L) was treated with potassium carbonate (184 g, 1.33 mol) and benzyl chloride 169 g, 1.34 mol). The mixture was heated at reflux overnight and concentrated to about half the volume under vacuum. Aqueous 5N NaOH (100 mL) was added, and the mixture was stirred at ambient temperature overnight and then concentrated. The residue was acidified with concentrated HCl. The yellow sold was collected by filtration and dried overnight under vacuum at 50° C. The crude product in isopropanol (1.8 L) was heated at reflux for about 30 minutes, cooled to ambient temperature, and stirred for about 16 hours. The slurry was filtered and dried under vacuum at 70° C. overnight to give the title compound as a white solid (137 g, 76%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated to about half the volume under vacuum
  4. additionAqueous 5N NaOH (100 mL) was added
  5. concentrationconcentrated
  6. filtrationThe yellow sold was collected by filtration
  7. customdried overnight under vacuum at 50° C
  8. temperatureThe crude product in isopropanol (1.8 L) was heated
  9. temperatureat reflux for about 30 minutes
  10. temperaturecooled to ambient temperature
  11. stirringstirred for about 16 hours
  12. filtrationThe slurry was filtered
  13. customdried under vacuum at 70° C. overnight

Sources & evidence

ORD record
ord-3cb6745777074114a96f265b51001818
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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