1-Octanol → Glycidyl n-octyl ether

HRID 842320Notes

Reaction equation

HRID 842320 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:10]([CH:12]1[O:14][CH2:13]1)Cl.[OH-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].[Al+3].S(=O)(=O)(O)O>[CH2:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:12]1[O:14][CH2:13]1

Participants

6

Procedure

Octanol (195 g, 1.5 mole), 1.02 g (0.005 mole) of aluminum triisopropoxide and 0.7 g (0.007 mole) of 98% sulfuric 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 then 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 95%. 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 175 g of octyl glycidyl ether (1,2-epoxy-4-oxadodecane) was obtained (total yield: 95%.).

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-ffe5d81414c8468f955fdb706a07f59f
Source dataset
uspto-grants-2002_04
Patent number
US06372923B1

Reaction notes

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