Chloral → HCID 12876713, compound

HRID 2287251Notes

Reaction equation

HRID 2287251 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, compoundYield 116.6%

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 4N hydrochloric acid (10 ml) and water (10 ml). After drying, the solvent was removed under reduced pressure to give 0.81 g (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 Hq).

Workup

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

Sources & evidence

ORD record
ord-866ae404964b4c2481a321da0272d9b8
Source dataset
uspto-grants-1981_05
Patent number
US04270000

Reaction notes

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