Ethanol → 8-Hydroxyjulolidine

HRID 2303941

Reaction equation

HRID 2303941 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 39%

Procedure

According to a procedure similar to that of Embodiment 5, a mixture of m-aminophenol (5.0 g, 45.8 mmol), 1-bromo-3-chloropropane (23.9 g, 15 ml, 150 mmol) and ethanol (50 ml) was heated and refluxed. NaHCO3 (10.0 g, 119 mmol) aqueous solution (20 ml) was added slowly. After 24 hours of reflux, 3.4 g of 8-hydroxyjulolidine was obtained in 39% yield.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed
  3. temperatureAfter 24 hours of reflux

Sources & evidence

ORD record
ord-a5fd6cbee54040239240a353d2500eff
Source dataset
uspto-grants-2002_08
Patent number
US06433176B1

Linked notes

Loading…