Hydrochloric Acid → Methyl 4-formylcyclohexane-1-carboxylate

Participants

Reaction Steps

103 g of methyl 4-methoxymethylidene-cyclohexane carboxylate was dissolved in 350 mL of THF, and 100 mL of 10% hydrochloric acid was added dropwise thereto at 11 to 13° C. for 10 minutes. The solution was further stirred at room temperature for 3 hours, and then 80 mL of hexane was added. The aqueous layer was extracted with ethyl acetate, and then the organic layers were combined and washed with water and saturated saline in this order. The resultant product was dried over anhydrous magnesium sulfate, and then concentrated, to obtain 92.4 g of methyl 4-formylcyclohexane carboxylate in the form of an oil-like product. The obtained product was analyzed by gas chromatography, and was found to be a mixture of cis-form:trans-form at a ratio of 64:36.

Provenance & Evidence