Hydrochloric Acid → HCID 11287251, compound

Participants

Reaction Conditions

Reaction Steps

A four-neck flask equipped with a thermometer, stirrer and condenser tube was charged with a tetrahydrofuran solution of vinylmagnesium (1.31 mol), and toluene (600 ml) was added to the solution. At 0° C., a toluene solution of 2-chlorocyclododecanone (159 g, 0.735 mol) was added dropwise to the solution, for reaction for 1 hour. After completion of reaction, 16% hydrochloric acid (120 g) was added for hydrolysis, and the solution was separated to take out the organic layer. The organic layer was washed with 2% sodium hydroxide aqueous solution (320 ml). To the obtained toluene solution, added were 30% sodium hydroxide aqueous solution (370 g, 2.78 mol) and benzyltriethylammonium chloride (1.86 g 0.00816 mol), and the mixture was stirred for reaction at 95° C. for 6 hours. After completion of reaction, the solution was separated to take out the organic layer, and the organic layer was washed with a saline solution. The solvent was distilled away under reduced pressure, and the residue was distilled for purification under reduced pressure, to obtain 133 g of a distillate. It was analyzed by means of capillary gas chromatography and found to be a mixture containing 61% of cis-1-vinyl-13-oxabicyclo[10.1.0]tridecane and 37% of trans-1-vinyl-13-oxabicyclo[10.1.0]tridecane (yield was 85%). The distillate was partially separated by means of silica gel chromatography for isolation into trans-1-vinyl-13-oxabicyclo[10.1.0]tridecane and cis-1-vinyl-13-oxabicyclo[10.1.0]tridecane.

Provenance & Evidence