Diethyl Ether → HCID 19863425, compound

HRID 1164940Notes

Reaction equation

HRID 1164940 reaction equation
[CH2:1]([OH:5])[CH:2]([CH3:4])[CH3:3].[CH2:6]([CH:8]1[O:10][CH2:9]1)Cl.C([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C.[OH-].[Na+].[CH3:23][CH2:24]OCC>[Cl-].[Cl-].[Zn+2]>[CH2:23]([CH:6]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]([OH:10])[CH2:9][O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[CH3:24]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6560IsobutanolHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 84352N-Ethylbenzylamine

Product 1

HCID 19863425HCID 19863425, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
100 °C

Procedure

To 100 mL (1.1 mol) of isobutanol under nitrogen atmosphere add 59 g (0.64 mol) of epichlorohydrin and ZnCl2 (1 mL of a 0.872 M solution in Et2O) Stir the reaction mixture at 100° C. for two days, then cool to room temperature and add 91 g (0.67 mol) of ethyl(phenylmethyl)amine and 100 mL of 50% aqueous NaOH. Resume heating for an additional three h. Add water and extract twice with Et2O. Combine the organic layers and dry over anhydrous Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Distillation of the residue (130° C. at 0.4 mm of Hg) provides the title compound.

Workup

  1. temperaturecool to room temperature
  2. temperatureResume heating for an additional three h
  3. extractionAdd water and extract twice with Et2O
  4. dry with materialdry over anhydrous Na2SO4
  5. customRemove the drying agent
  6. filtrationby filtration
  7. customremove the solvent in vacuo
  8. distillationDistillation of the residue (130° C. at 0.4 mm of Hg)

Sources & evidence

ORD record
ord-25c2dc5b614a498bb61311c457e61298
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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