1-Octanol → Glycidyl n-octyl ether

HRID 2304977Notes

Reaction equation

HRID 2304977 reaction equation
[B].[CH2:2]([CH:4]1[O:6][CH2:5]1)Cl.[CH2:7]([OH:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[CH2:2]([O:15][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:4]1[O:6][CH2:5]1

Participants

4

Conditions

Temperature
0 °C

Procedure

Octanol (130 g) and 2.84 g of a boron trifluorideether complex were cooled to 0° C. while stirring. At a temperature maintained at 0° C., 138.8 g of epichlorohydrin was added dropwise over 1 hour. After completion of dropwise addition, an excess alcohol was distilled off at 100° C. under reduced pressure (13 to 26 Pa). The reaction mixture was cooled to 50° C. and while maintaining the temperature at 50° C., 125 g of a 48% aqueous solution of sodium hydroxide was added dropwise over 1 hour. After stirring for 3 hours, 200 mL of water was added to the reaction mixture to cause separation. The water layer thus obtained was removed and then the residue was washed twice with 100 mL of water, whereby 208 g of crude octyl glycidyl ether was obtained.

Workup

  1. additionAfter completion of dropwise addition
  2. distillationan excess alcohol was distilled off at 100° C. under reduced pressure (13 to 26 Pa)
  3. temperatureThe reaction mixture was cooled to 50° C.
  4. temperaturewhile maintaining the temperature at 50° C.
  5. addition125 g of a 48% aqueous solution of sodium hydroxide was added dropwise over 1 hour
  6. stirringAfter stirring for 3 hours
  7. addition200 mL of water was added to the reaction mixture
  8. customseparation
  9. customThe water layer thus obtained
  10. customwas removed
  11. washthe residue was washed twice with 100 mL of water

Sources & evidence

ORD record
ord-1d6273ad3b1349c3b3cc5b157232fe13
Source dataset
uspto-grants-2002_08
Patent number
US06437196B1

Reaction notes

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