p-Toluenesulfonic acid → tetradecahydrocyclododeca[b]furan

Participants

Reaction Steps

The toluene solution of the diol from step 5 (approximately 0.59 mol) was mixed with 12 gm of p-toluenesulfonic acid and heated with agitation for approximately 4 hours under a water separator. After the reaction was complete, the mixture was neutralized with 5% sodium hydroxide solution, the aqueous phase was separated, and the toluene phase was evaporated. Approximately 80 gm of 13-oxabicyclo[10.3.0]pentadecane (65% yield) were isolated by vacuum distillation at 90° to 95° C./0.25 mbar.

Provenance & Evidence