Hydrogen Bromide → 4,4-Dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol

Participants

Reaction Steps

A mixture of 4,4-dimethyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (23.9 g, 0.125 mol) and 48% aqueous hydrobromic acid (158 ml) were heated at vigorous reflux for 4 hours. The reaction mixture was cooled and evaporated in vacuo. The residue was triturated with diethyl ether (20 ml), 1:1 diethyl ether:thf (20 ml) and diethyl ether (3×20 ml) and dried in vacuo to afford the title compound as the hydrobromide salt (17.5 g, 53%).

Provenance & Evidence