(S)-2-methoxycyclohexanol → (S)-2-Methoxycyclohexanone

HRID 430019

Reaktionsgleichung

Reaktionsgleichung von HRID 430019
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[OH:9].S([O-])(O)=O.[Na+]>>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]

Komponenten

3

Edukt 2

HCID 12574977(S)-2-methoxycyclohexanolHCID 23665763Sodium Bisulfite

Produkt 1

HCID 642158(S)-2-Methoxycyclohexanone

Versuchsvorschrift

Reaction was carried out in the same manner as in Example 16. After the peak due to (S)-2-methoxycyclohexanol had disappeared, the reaction solution was given 2 g of sodium hydrogensulfite with stirring so that the reaction solution did not change potassium iodide starch paper into purple any longer. The reaction solution was extracted twice with 100 g of dichloroethane. The dichloroethane layers were combined together and washed with a saturated aqueous solution of sodium chloride. After concentration and distillation in the same manner as in Example 1, there was obtained 10.9 g (85 mmol) of (S)-2-methoxycyclohexanone having a chemical purity of 99.4% and an optical purity of 99.5% ee (measured immediately after distillation). As in Example 3, this product was sealed in a glass ample, with the atmosphere therein replaced with argon. The glass ample was heated at a prescribed temperature for 20 hours. After cooling to room temperature, the ample was opened and the content was tested for optical purity. The results are shown in Table 3.

Aufarbeitung

  1. customReaction
  2. extractionThe reaction solution was extracted twice with 100 g of dichloroethane
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. concentrationAfter concentration and distillation in the same manner as in Example 1

Quellen und Nachweise

ORD-Eintrag
ord-972e9b0d19804fe68f9a4139fd143d3a
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320069B1

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