1-Pentanol → 2-(Pentoxymethyl)oxirane

HRID 2304979Notes

Reaction equation

HRID 2304979 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+]>[Cl-].[Zn+2].[Cl-].O>[CH2:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:9]1[O:11][CH2:10]1

Participants

6

Conditions

Temperature
115 °C

Procedure

n-Pentanol (88 g) and 6.82 g of zinc chloride were heated to 100° C. while stirring, followed by the dropwise addition of 138.8 g of epichlorohydrin over 1 hour. The reaction mixture was heated to 115° C. and reacted for 5 hours. After completion of the reaction, the reaction mixture was cooled to 50° C. While maintaining the temperature at 50° C., 92 g of a 48% aqueous solution of sodium hydroxide was added dropwise over 1 hour. After stirring for 3 hours, 150 mL of water was added to the reaction mixture to cause separation. The water layer thus formed was then removed and the residue was washed twice with 100 mL of water, whereby 163 g of crude pentyl glycidyl ether was obtained.

Workup

  1. customreacted for 5 hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to 50° C
  4. temperatureWhile maintaining the temperature at 50° C.
  5. stirringAfter stirring for 3 hours
  6. customseparation
  7. customThe water layer thus formed
  8. customwas then removed
  9. washthe residue was washed twice with 100 mL of water

Sources & evidence

ORD record
ord-6f0cfc57c7c04304a3a88339e331ae69
Source dataset
uspto-grants-2002_08
Patent number
US06437196B1

Reaction notes

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