[3-(Hydroxymethyl)-1-adamantyl]methanol → HCID 15483193, compound

Participants

Reaction Steps

To a suspension of pyridinium chlorochromate (PCC, 0.850 g, 4.0 mmol) in CH2Cl2 (˜10 mL) was added a suspension of 1,3-bis(hydroxymethyl)adamantane (0.196 g, 1.0 mmol) in anhydrous THF (˜5 mL). The reaction mixture was stirred at room temperature for 2.5 hours, whereupon it was diluted with anhydrous diethyl ether (˜50 mL) and filtered through a plug of florisil. The filtrate was evaporated in vacuo to afford dicarbaldehyde (0.183 g, 95%). According to GC analysis (DB 210, 150° C.), product had a purity of over 95%. Since dialdehyde is unstable and decomposes on silica gel, the sample was used in the next step without further purification.

Provenance & Evidence