Hydrochloric Acid → HCID 15279122, compound

Participants

Reaction Steps

Into a 200 milliliter Erlenmeyer flask, 38.37 grams (183.3 millimoles) of 2-cyano-2-trimethylsiloxynorbornane obtained in A, a PTFE-coated stirrer bar, 30 milliliters of tetrahydrofuran, 10 milliliters of water, and 1 milliliter of 2N hydrochloric acid were placed. This mixture was vigorously stirred at room temperature. Three hours later, the disappearance of the starting norbornane compound was confirmed by thin-layer chromatography, and 1 milliliter of 2N aqueous potassium hydrogencarbonate solution was then added to the reaction mixture and the mixture was vigorously stirred for 5 minutes. The reaction mixture was poured into water and extracted three times with diethyl ether, and the extracts were combined, washed with brine, and dried with anhydrous sodium sulfate. The sodium sulfate was then filtered out. The solvent was subsequently removed in vacuo to thereby yield a crude product. Distillation of the crude product under reduced pressure gave 2-cyano-2-hydroxynorbornane (exo/endo mixture) as a colorless, clear liquid having a boiling point of 85.5°-86.0° C. (0.35 mmHg).

Provenance & Evidence