Hydrochloric Acid → HCID 13534072, compound

Participants

Reaction Conditions

Reaction Steps

para-Toluenesulfonyl chloride (15.5 g,) was added portionwise over 20 minutes to an ice-cold stirred solution of 1,5-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-ol (10.0 g,) in dry pyridine (75 ml). The reaction mixture was stirred at 0° C. for 0.5 hour, allowed to stand in a refrigerator (0° C.) for 72 hours, and poured into a mixture of 80 ml concentrated hydrochloric acid and 100 g of ice. After stirring for 10 minutes, the precipitated solid was filtered. The collected solid dissolved methylene chloride was dried (MgSO4), filtered and concentrated to give 17.6 g (88%) of the desired product, m.p. 75°-77° C., as a 70:30 mixture of epimers.

Provenance & Evidence