1-Ethynylcyclohexanol → 1-Ethynylcyclohexyl methyl carbonate

Participants

Reaction Steps

A solution of 36.0 gm of 1-ethynylcyclohexanol in 50 ml of benzene was slowly added drop-by-drop to an agitated suspension, cooled to 0° to 5° C., of 5.5 gm of finely distributed sodium in 50 ml of absolute toluene and 250 ml of benzene, and was agitated at room temperature until reaction had been completed. 26.0 gm of methyl chloroformate were added under cooling to the sodium salt which has been formed. The mixture was allowed to react for 12 hours at room temperature and was washed several times with water and dried. After distilling off the solvent, the raw ester was fractionated by means of a 20 cm Vigreux column. The methyl 1-ethynylcyclohexyl carbonate thus obtained constitutes a coloroless liquid having a fruity, herbal, complex odor and a distinctive fragrance of dill, and has the following characteristic values:

Provenance & Evidence