Hydrochloric Acid → 1-Methoxy-1,3,5-cycloheptatriene

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Reaction Steps

In the first step of the above synthesis, warm water is used to dissolve the cycloheptatrienyl tetrafluoborate (tropylium tetrafluoborate) (I) salt under a nitrogen atmosphere. Methanol is added to the resulting aqueous solution of (I), followed by the addition of solid sodium bicarbonate to give the reaction product 7-methoxycycloheptatriene (II). The 7-methoxycycloheptatriene (II) is isomerized by heating at 150° C. for two hours to produce 3-methoxycycloheptatriene (III). In the third step, 3-methoxycycloheptatriene (III) is isomerized in an acid catalyzed rearrangement utilizing hydrogen chloride in methanol at room temperature for two hours, followed by neutralization with sodium bicarbonate, filtration and fractional distillation to give the product 1-methoxycycloheptatriene (IV).

Provenance & Evidence