Ethylene Glycol → 2-[(Benzyloxy)methyl]-5,8-dioxaspiro[3.4]octane

HRID 1966813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966813
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][CH2:20][CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:26](O)[CH2:27][OH:28].O>C1C=CC=CC=1>[CH2:12]([O:19][CH2:20][CH:21]1[CH2:24][C:23]2([O:28][CH2:27][CH2:26][O:25]2)[CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 118198503-((Benzyloxy)methyl)cyclobutanone

Produkt 1

HCID 120735822-[(Benzyloxy)methyl]-5,8-dioxaspiro[3.4]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

p-Toluene sulphonic acid (2.0 gm) was added to a solution of 3-[(benzyloxy)methyl]cyclobutanone (25.0 gm, 131.6 mmol) (step b) and 1,2-ethanediol (8.98 gm, 144.7 mmol) in benzene and the reaction mixture was refluxed with removal of water through dean-stark apparatus. After about 6 hours, the reaction mixture was cooled to room temperature and washed with saturated sodium bicarbonate solution, followed by water and brine. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to get a crude product, which was purified by column chromatography.

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b23567b64d20417a92136be82466d129
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420666B2

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