Ethylene Glycol → Ethyl 2-methyl-1,3-dioxolane-2-propionate

HRID 235702

Reaktionsgleichung

Reaktionsgleichung von HRID 235702
[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:16]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:17][CH2:18][C:19]([CH3:21])=O.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[CH2:1]1[O:4][C:19]([CH3:21])([CH2:18][CH2:17][C:16]([O:23][CH2:24][CH3:25])=[O:22])[O:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 10883Ethyl levulinateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 70332Ethyl 2-methyl-1,3-dioxolane-2-propionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of about 110.86 g of ethylene glycol, about 2 g of p-toluenesulfonic acid and about 800 ml of toluene was refluxed using a Dean-Stark trap until no more water came off. An about 250 g portion of ethyl levulinate was added and refluxing was continued until no more water came off. The mixture was then cooled to room temperature, poured into saturated sodium bicarbonate, the organic layer dried and the solvent removed. The residue was distilled (about 67°-70° C., 0.35 mm) and the distillate stirred for about 20 minutes with about 6 g of sodium borohydride in ethanol. The solvent was removed, the residue dissolved in ether, washed with saturated sodium bicarbonate, dried and then distilled (about 41°-45° C., 0.3 mm), giving about 83 g of the desired title compound.

Aufarbeitung

  1. temperaturewas refluxed
  2. temperaturerefluxing
  3. customthe organic layer dried
  4. customthe solvent removed
  5. distillationThe residue was distilled (about 67°-70° C., 0.35 mm)
  6. customThe solvent was removed
  7. dissolutionthe residue dissolved in ether
  8. washwashed with saturated sodium bicarbonate
  9. customdried
  10. distillationdistilled (about 41°-45° C., 0.3 mm)

Quellen und Nachweise

ORD-Eintrag
ord-2ae60c5edcd243dd857201c80ff05cdc
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

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