1-Propanol → HCID 19437279, compound

HRID 359785Notes

Reaction equation

HRID 359785 reaction equation
[CH2:1](Cl)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][CH:26]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[N:11]=1.[OH-].[Na+].ClCCl.[CH2:32](O)[CH2:33][CH3:34]>>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][CH:26]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:34][CH:33]=[CH2:32])[CH:18]=2)[N:11]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 5

HCID 10311-PropanolHCID 6344DichloromethaneHCID 7850Allyl chlorideHCID 14798Sodium HydroxideHCID 20064236HCID 20064236, compound

Product 1

HCID 19437279HCID 19437279, compoundYield 90%

Procedure

59.7 g allyl chloride were added dropwise at 95° C. to a solution of 87.9 g of 2,6-bis-(3-hydroxyphenoxy)-pyridine (prepared according to DE-A 19 34 889 from 2,6-dichloropyridine and 2 moles of resorcinol; colorless crystals of melting point 188° C.) and 26.4 g of sodium hydroxide in 500 ml of n-propanol. The mixture was refluxed for a further 10 hours and then cooled to room temperature, after which 500 ml of dichloromethane were added and the precipitated sodium chloride was filtered off. After the solvent had been distilled off under reduced pressure, 101 g (90%) of product were obtained as a yellowish oil having a viscosity of 60 mPa.s at 50° C.; NMR (300 MHZ, D6-DMSO): 4.56 (d, 4H, allyl), 5.22-5.42 (dd, 4H, allyl), 5.95-6.10 (m, 2H, allyl), 6.60-6.85 (m, 6H, arom.), 7.22 (t, 2H, arom.), 7.82 (t, 1H, arom.).

Workup

  1. temperatureThe mixture was refluxed for a further 10 hours
  2. filtrationthe precipitated sodium chloride was filtered off
  3. distillationAfter the solvent had been distilled off under reduced pressure

Sources & evidence

ORD record
ord-453c69d240e74373ac13e357512e921d
Source dataset
uspto-grants-1991_03
Patent number
US05003017

Reaction notes

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