p-Toluenesulfonic acid → 2-(2-Benzyloxyethoxy)-cyclohexanone

HRID 1654487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654487
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[CH2:9]([O:16][CH:17](O)[CH3:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:9]([O:16][CH2:17][CH2:18][O:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1=[O:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 10785Cyclohexanone, 2-hydroxy-HCID 19595026Benzyloxyethanol

Produkt 1

HCID 200779602-(2-Benzyloxyethoxy)-cyclohexanoneAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of dimeric 2-hydroxycyclohexanone (13.7 g), 2 benzyloxyethanol (20 g) and p-toluensulphonic acid (2 g) were dissolved in xylene (500 ml) in a round bottom flask fitted with a Dean Stark apparatus and reluxed for 10 hrs. The resulting solution was cooled, washed with sodium hydrogen carbonate (3×50 ml) dried and concentrated under reduced pressure. The crude oil was then purified by flash chromatography using cyclohexane/ethyl acetate 60/40 as eluant yielding 20 g of the title compound (Rf=0.5).

Aufarbeitung

  1. customfitted with a Dean Stark apparatus
  2. temperatureThe resulting solution was cooled
  3. washwashed with sodium hydrogen carbonate (3×50 ml)
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude oil was then purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-465f23e0acd14dcb8bd9ce9fcb10622f
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407931

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