Chloral → 1-[(4-Hydroxyphenyl)methyl]-3,4,5,6,7,8-hexahydroisoquinoline-2(1H)-carbaldehyde

Participants

Reaction Steps

To a mixture of 30.0 g (0.12 mol) of (±)-1-(p-hydroxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline and 75 ml of chloroform was added dropwise to a solution of 19.2 g of trichloroacetaldehyde in 30 ml of chloroform. After the mixture had been stirred for 16 hrs at room temperature it was diluted with 150 ml of chloroform and washed with 4 N aqueous hydrochloric acid (50 ml) and water (50 ml). After drying, the solvent was removed under reduced pressure to give a residue, which after crystallization from ethyl acetate afforded 33.1 g (98%) of pure (±)-1-(p-hydroxybenzyl)-2-formyl-1,2,3,4,5,6,7,8-octahydroisoquinoline, mp 154°-156°. For analysis a sample of this compound was recrystallized from ethyl acetate, mp 161°-162°.

Provenance & Evidence