Ethylene Glycol → HCID 12869104, Verbindung

HRID 73622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73622
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])=[O:4].[CH2:12](O)[CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:14]1[C:6]2([CH2:7][CH2:8][CH2:9][CH2:10][CH:5]2[C:3]([O:2][CH3:1])=[O:4])[O:11][CH2:12][CH2:13]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 170489Cyclohexanecarboxylic acid, 2-oxo-, methyl esterHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 12869104HCID 12869104, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of methyl-2-oxocyclohexanecarboxylate (4-1) (7.0 g, 44.8 mmol), ethylene glycol (3.00 mL, 53.8 mmol) and p-toluenesulfonic acid monohydrate (0.853 g, 4.48 mmol) in Benzene (45 mL) was heated to reflux overnight. The reaction was then cooled to rt and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.86-3.99 (m, 4H), 3.69 (s, 3H), 2.69 (dd, 1H, J=4.9 Hz, 9.0 Hz), 1.82-1.97 (m, 3H), 1.58-1.73 (m, 3H), 1.45-1.53 (m, 1H), 1.26-1.37 (m, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e941809fc46f44f69bbcda672120d6df
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829196B2

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