1-Pentanol → 2-(Pentoxymethyl)oxirane

HRID 842321Notes

Reaction equation

HRID 842321 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:7]([CH:9]1[O:11][CH2:10]1)Cl.[OH-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].[Al+3].C1C(O)=CC=C(S(O)(=O)=O)C=1>[CH2:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:9]1[O:11][CH2:10]1

Participants

6

Reactant 3

HCID 62761-PentanolHCID 7835Epichlorohydrin2×HCID 14798Sodium Hydroxide

Product 1

HCID 1389782-(Pentoxymethyl)oxiraneYield 86%

Reagents, catalysts & solvents 2

HCID 47654-Hydroxybenzenesulfonic acidCatalystHCID 11143Aluminum isopropoxideCatalyst

Procedure

Amyl alcohol (132 g, 1.5 mole), 1.02 g (0.005 mole) of aluminum triisopropoxide and 2.64 g (0.015 mole) of p-phenolsulfonic acid were heated to 90° C. while stirring under a nitrogen gas atmosphere. To the reaction mixture, 92.5 g (1.0 mole) of epichlorohydrin was added dropwise over 1 hour, followed by stirring for 4 hours. It was found that the conversion ratio of the raw material epichlorohydrin was 100%, while the yield of the resulting halohydrin ether was 87%. To the reaction mixture, 300 mL of a 4N aqueous solution of sodium hydroxide was added and the resulting mixture was stirred at 60° C. for 6 hours. After cooling to room temperature, the water layer was removed and the residue was purified by distillation under reduced pressure, whereby 124 g of amyl glycidyl ether (1,2-epoxy-4-oxanonane) was obtained (total yield: 86%).

Workup

  1. stirringby stirring for 4 hours
  2. stirringthe resulting mixture was stirred at 60° C. for 6 hours
  3. customthe water layer was removed
  4. distillationthe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-70cccd0d11e942d1a6642077476637e2
Source dataset
uspto-grants-2002_04
Patent number
US06372923B1

Reaction notes

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