Ethanol → 8-Hydroxyjulolidine

HRID 2303940

Reaction equation

HRID 2303940 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][CH2:12]Cl.[C:14]([O-])(O)=O.[Na+].[CH2:19](O)[CH3:20]>>[CH2:11]1[CH2:12][N:1]2[C:2]3[C:3]([CH2:14][CH2:19][CH2:20]2)=[C:4]([OH:8])[CH:5]=[CH:6][C:7]=3[CH2:10]1

Participants

5

Reactant 4

HCID 702EthanolHCID 80061-Bromo-3-chloropropaneHCID 115683-AminophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 1704748-HydroxyjulolidineYield 35%

Procedure

m-Aminophenol (1.1 g, 10 mmol), 1-bromo-3-chloropropane (4.8 g, 3 ml, 30 mmol) and ethanol (10 ml) were placed in a 100 ml two-necked round-bottomed flask. The mixture was heated and refluxed for 11 hours, during which an NaHCO3 aqueous solution (2.0 g, 20 ml, 23 mmol) was added. The mixture was further heated and refluxed for 37 hours. The solvent was removed by distillation under reduced pressure. The resulting crude product was extracted with hexane by a solid-liquid continuous extraction to give 8-hydroxyjulolidine (661 mg) in 35% yield.

Workup

  1. temperatureThe mixture was heated
  2. additionwas added
  3. temperatureThe mixture was further heated
  4. temperaturerefluxed for 37 hours
  5. customThe solvent was removed by distillation under reduced pressure
  6. extractionThe resulting crude product was extracted with hexane by a solid-liquid continuous extraction

Sources & evidence

ORD record
ord-e3674b5e94114bc79142154a9fbf5eb4
Source dataset
uspto-grants-2002_08
Patent number
US06433176B1

Linked notes

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