Oxalic Acid → HCID 86735843, compound

Participants

Reaction Steps

Adamantane-1-isopropyl alcohol (50 gm.), 20.6 ml. pyridine, 10.3 ml. trifluoroacetic acid, 387 ml. benzene, and 387 ml. dimethylsulfoxide were added to a reaction flask and 159 gm. dicyclohexylcarbodiimide was added over 5 minutes. The mixture was stirred overnight, a solution of 70 gm. oxalic acid in 650 ml. methanol added, and the reaction mixture left 1 day at room temperature. The solution was mixed with 4 liters of water, stirred several hours, filtered and the ether separated, washed, dried and concentrated. The ether residue was taken up in a small amount of ether, filtered to remove solid, concentrated and distilled to give 37 gm. b0.025 64°-73°.

Provenance & Evidence