Chloral → HCID 12876713, compound

HRID 1390105Notes

Reaction equation

HRID 1390105 reaction equation
[O:1]([C:8]1[CH:24]=[CH:23][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][NH:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:25]=[CH:26]C(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[O:1]([C:8]1[CH:24]=[CH:23][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:26]=[O:25])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6407ChloralHCID 12876712HCID 12876712, compound

Product 1

HCID 12876713HCID 12876713, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of 0.78 g (0.002 mol) of (±)-1-(p-phenoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline in 5 ml of chloroform was added 0.42 g of chloral in 1 ml of chloroform dropwise. After the mixture had been stirred at room temperature for 3 hrs it was diluted with 15 ml of chloroform and washed with 4 N hydrochloric acid (10 ml) and water (10 ml). After drying, the solvent was removed under reduced pressure to give 0.81 (96%) of crude (±)-1-(p-phenoxybenzyl)-2-formyl-1,2,3,4,5,6,7,8-octahydroisoquinoline. For characterization, a sample of this compound was distilled, bp 225°-227° (0.08 mm Hg).

Workup

  1. washwashed with 4 N hydrochloric acid (10 ml) and water (10 ml)
  2. customAfter drying
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f3d1b77667a84df79b05a032d7725d2b
Source dataset
uspto-grants-1981_01
Patent number
US04247697

Reaction notes

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