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

Participants

Reaction Steps

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.

Provenance & Evidence