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

HRID 459192노트

반응식

HRID 459192 반응식
[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

참가 물질

5

반응물 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 9920545Latifolicinin C acid

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-3cb6745777074114a96f265b51001818
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192982B2

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