Cyclohexene oxide → HCID 67266608, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, 4 ml of 1,1,1,3,3,3-hexafluoro isopropanol and 12 ml of acetonitrile were added to L-ascorbic acid (1.00 g), and further, 1,2-epoxycyclohexane (1.42 g) was added. The mixture was heated up to 70° C. and stirred for 36 hours, then, concentrated under reduced pressure, and 3.65 g of the resultant residue was subjected to silica gel column chromatography. Thereafter, it was eluted with chloroform/methanol/water(volume ratio:20/3/0.3) to obtain two elution fractions (first eluted fraction: 244 mg, later eluted fraction: 217 mg). Based on the measurement results of high resolution mass analysis, infrared absorption spectrum, 1H-NMR, 13C-NMR and specific optical rotation on the resultant elution fractions, it was confirmed that these are two 3-O-(2-hydroxycyclohexyl) ascorbic acids which are in mutual stereoisomerism and both of them are represented by the following structural formula.

Provenance & Evidence