Ethylene Glycol → 3,3-Ethylenedioxy-1-phenylcyclohexanecarbonitrile

HRID 1178855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178855
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:8]#[N:9])[CH2:3]1.[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH2:16]1[CH2:17][O:18][C:2]2([CH2:7][CH2:6][CH2:5][C:4]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)([C:8]#[N:9])[CH2:3]2)[O:1]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 123391223-Oxo-1-phenylcyclohexanecarbonitrile

Produkt 1

HCID 123391803,3-Ethylenedioxy-1-phenylcyclohexanecarbonitrileAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
111 °C

Versuchsvorschrift

The mixture of 3-oxo-1-phenylcyclohexanecarbonitrile (2.62 g), ethylene glycol (3.65 mL) and pyridinium p-toluene sulfonate (1 spatula) in benzene (40 mL) was stirred at 111° C. with Dean-Stark apparatus overnight. After cooling down to room temperature, the mixture was washed with saturated sodium bicarbonate and the organic layer was separated. The aqueous layer was extracted with dichloromethane 3 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude material was purified by Flash Chromatography with from 25% ethyl acetate/75% hexane to 30% ethyl acetate/70% hexane over 20 minutes. The title compound was obtained as a white solid (1.66 g, 48% yield in 2 steps). 1H NMR (400 MHz, CDCl3) δ 1.56 (1H, dt, J=4, 16 Hz), 1.70-1.79 (1H, m), 1.89-1.96 (3H, m), 2.06-2.28 (3H, m), 3.89-3.97 (2H, m), 4.03-4.12 (2H, m), 7.28-7.32 (1H, m), 7.36-7.39 (2H, m), 7.48-7.51 (2H, m). HPLC purity (retention time): 95% (1.62 min, method C). MS: 266.37 (M+Na+).

Aufarbeitung

  1. temperatureAfter cooling down to room temperature
  2. washthe mixture was washed with saturated sodium bicarbonate
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane 3 times
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude material was purified by Flash Chromatography with from 25% ethyl acetate/75% hexane to 30% ethyl acetate/70% hexane over 20 minutes

Quellen und Nachweise

ORD-Eintrag
ord-6db3cc68833a4f6495708a2f1a8f91df
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276631B2

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