Phosphoric Acid → HCID 22810374, compound

Reaction equation

[O:1]([C:8]1[CH:26]=[CH:25][C:11]([CH2:12][CH:13]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[CH2:16][CH2:15][N:14]2[CH:23]=[O:24])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(=O)(O)(O)O.S(=O)(=O)(O)O>>[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[N:14]([CH:23]=[O:24])[CH2:15][CH2:16][C@@:17]4([C:25]=2[CH:26]=1)[C@H:22]3[CH2:21][CH2:20][CH2:19][CH2:18]4)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 1004Phosphoric Acid

HCID 1118Sulfuric Acid

HCID 12876713HCID 12876713, compound

Product 1

HCID 22810374HCID 22810374, compoundYield 95%

Procedure

(±)-1-(p-Phenoxybenzyl)-2-formyl-1,2,3,4,5,6,7,8-octahydroisoquinoline, 24.5 g (0.07 mol), was combined under stirring with 120 g of phosphoric acid which had been mixed with 1.0 g of concentrated sulfuric acid and the mixture was heated in a nitrogen atmosphere to 70°. The resulting homogeneous solution was kept at 70° for 48 hrs. The mixture was cooled in an ice bath and ice-water was added. The resulting suspension was extracted with ethyl acetate (100 ml). The ethyl acetate solution was washed with water and dried. Removal of the solvent gave 23.3 g (95%) of crude (±)-3-phenoxy-N-formylmorphinan.