Potassium Hydroxide → 2,2-Dimethyl-4-(oxiran-2-YL)-1,3-dioxolane

HRID 1589414Notes

Reaction equation

HRID 1589414 reaction equation
Cl[CH:2]([CH:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6]1)[CH2:3][OH:4].[OH-].[K+]>CCOCC>[CH3:10][C:7]1([CH3:11])[O:6][CH:5]([CH:2]2[O:4][CH2:3]2)[CH2:9][O:8]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 131868262-Chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

Product 1

HCID 131868272,2-Dimethyl-4-(oxiran-2-YL)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

340 g of 2-chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol is dissolved in 1.5 l of absolute ether. At 5° C., a total of 130 g of pulverized potassium hydroxide is added under intensive agitation within 30 minutes, while the temperature is maintained between 5° and 15° C. by cooling. The suspension is then heated at 40° C. for 2 hours under gentle refluxing. After heater and agitator have been turned off, the phases begin to separate. After allowing the mixture to stand overnight, it is vacuum-filtered over kieselguhr. The residue is extracted with ether. The combined ether extracts are concentrated over a 60 cm Vigreux column. The residue (260 g) is distilled under vacuum, during which step 180 g of a colorless liquid passes over; this liquid is fractionated, yielding 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethylene oxide at 65° C./13 mm.

Workup

  1. temperatureis maintained between 5° and 15° C.
  2. temperatureby cooling
  3. customto separate
  4. filtrationit is vacuum-filtered over kieselguhr
  5. extractionThe residue is extracted with ether
  6. concentrationThe combined ether extracts are concentrated over a 60 cm Vigreux column
  7. distillationThe residue (260 g) is distilled under vacuum, during which step 180 g of a colorless liquid

Sources & evidence

ORD record
ord-40db5b6358e64d549d7896a1934b401d
Source dataset
uspto-grants-1986_02
Patent number
US04570007

Reaction notes

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