Cyclopentadiene → HCID 70010430, compound

Participants

Reaction Steps

A thick walled, high pressure tube was charged with freshly cracked cyclopentadiene (0.841 g, 12.72 mmol) and 4-hydroxy-3-benzyloxy-2-butene (9.06 g, 50.92 mmol). The contents were degassed by bubbling nitrogen gas through the solution for 5 minutes. The tube was equipped with a magnetic stirring bar and fitted with a Teflon screw cap. The reaction tube was placed into a oil bath set at 185° C. and the starting materials were allowed to react for 48 hours. The tube was then taken out of the oil bath and allowed to cool to room temperature. The solution was transferred to a round bottom flask and the excess 1-Hydroxy-2-Benzyloxy-Butene distilled using vacuum distillation (105° C., 5 mmHg). The distillation yielded 3.48 grams of 1-Hydroxy-2-Benzyloxy-Butene. The remainder of the solution in the flask was treated with vacuum distillation yielding 1.924 grams (62%) of product at 189° C. (1 mmHg). The product was extracted using petroleum ether. The product was observed and it's identity confirmed by 1HNMR, 13CNMR, and HRMS.

Provenance & Evidence