Phosphoric Acid → HCID 22810374, compound

HRID 1701580Notes

Reaction equation

HRID 1701580 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

4

Reactant 3

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 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.

Workup

  1. temperaturethe mixture was heated in a nitrogen atmosphere to 70°
  2. temperatureThe mixture was cooled in an ice bath
  3. extractionThe resulting suspension was extracted with ethyl acetate (100 ml)
  4. washThe ethyl acetate solution was washed with water
  5. customdried
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-9274ff7cc5554d9bb3967b7e01579432
Source dataset
uspto-grants-1980_03
Patent number
US04194044

Reaction notes

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