Ethanol → 56469-01-3

HRID 462052Notes

Reaction equation

HRID 462052 reaction equation
[CH2:1]([OH:3])[CH3:2].[OH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2.C(C1[O:19][CH2:18]1)Cl>[Na]>[OH:3][CH:1]([CH2:18][OH:19])[CH2:2][O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 702EthanolHCID 19238-HydroxyquinolineHCID 7835Epichlorohydrin

Product 1

HCID 9186956469-01-3

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

To 100 ml of ethanol in which 2,5 g of sodium metal had been dissolved was added 15 g of 8-hydroxyquinoline. 12 g of epichlorohydrin was then added to the resulting solution and the mixture was refluxed for 8 hours while stirring. After completion of the reaction, the precipitated material was removed by filtration, and the mother liquor was concentrated to dryness. The resulting residue was recrystallized from ethanol-water to give 16 g of 8-(2,3-dihydroxy)propoxyquinoline as colorless needle-like crystals having a melting point of 193° - 194° C.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customAfter completion of the reaction
  3. customthe precipitated material was removed by filtration
  4. concentrationthe mother liquor was concentrated to dryness
  5. customThe resulting residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-9ded62a742d14626a1e774926bc8ed25
Source dataset
uspto-grants-1977_12
Patent number
US04065456

Reaction notes

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