Chloral → 1-[(4-Hydroxyphenyl)methyl]-3,4,5,6,7,8-hexahydroisoquinoline-2(1H)-carbaldehyde
Reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.ClC(Cl)(Cl)[CH:21]=[O:22]>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[CH2:10][CH2:9][N:8]2[CH:21]=[O:22])=[CH:17][CH:18]=1Participants
4
Procedure
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°.