p-Toluenesulfonic acid → Oxiranemethanol, 3-[(phenylmethoxy)methyl]-

HRID 400234

Reaktionsgleichung

Reaktionsgleichung von HRID 400234
C[O:2]C(OC)(C)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[O:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CC(C)=O.CCOCC>[CH2:18]([O:19][CH2:24][CH:23]1[O:22][CH:21]1[CH2:20][OH:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 312751,4-Dioxane

Produkt 1

HCID 3934498Oxiranemethanol, 3-[(phenylmethoxy)methyl]-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2,2-Dimethoxypropane (12 mL, 97 mmol) was added with stirring to a solution of crude diols A and B, catalytic p-toluenesulfonic acid in acetone (50 mL). The mixture was stirred at room temperature overnight, diluted with ether and washed with aqueous sodium bicarbonate solution (twice). The organic extract was dried (magnesium sulfate), filtered and concentrated. The crude oil was chromatographed on a silica gel column and eluted with 2-10% ethyl acetate in hexanes to obtain dioxane C (5.85 g, 65% overall yield from 4-benzyloxy-2,3-epoxy-1-butanol) as a colorless oil.

Aufarbeitung

  1. washwashed with aqueous sodium bicarbonate solution (twice)
  2. extractionThe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was chromatographed on a silica gel column
  7. washeluted with 2-10% ethyl acetate in hexanes
  8. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-ede2c44152fa49799c2be5af1e02fafb
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827868

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