Hydrogen Bromide → Undecane hydrobromide

Participants

Reaction Steps

D,L-2-aza-2'-hydroxy-5,6-benzotricyclo-[6.3.01,8.04,11 ]undecane (2.68 g; 11.7 mmoles) is refluxed under argon in a mixture of acetic acid (67 ml) and 47% hydrobromic acid (677 ml) for 50 hours. The mixture is evaporated to dryness. The residue is dissolved in hot methanol and evaporated onto 15 g silica gel which is then placed on top of 80 g silica gel. Elution with chloroform:methanol:ammonium hydroxide (100:15:1 v:v:v) yields D,L-2-aza-2'-hydroxy-5,6-benzotricyclo[6.3.01,8.04,11 ] undecane hydrobromide: 2.23 g; 89%; melting point: 284°-286° C.

Provenance & Evidence