Chloral → 1-[(4-Hydroxyphenyl)methyl]-3,4,5,6,7,8-hexahydroisoquinoline-2(1H)-carbaldehyde

HRID 1390102Notes

Reaction equation

HRID 1390102 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]=1

Participants

4

Reactant 2

HCID 6407ChloralHCID 145561084-[(1,2,3,4,5,6,7,8-Octahydroisoquinolin-1-yl)methyl]phenol

Product 1

HCID 234600991-[(4-Hydroxyphenyl)methyl]-3,4,5,6,7,8-hexahydroisoquinoline-2(1H)-carbaldehydeYield 101.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

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°.

Workup

  1. washwashed with 4 N aqueous hydrochloric acid (50 ml) and water (50 ml)
  2. customAfter drying
  3. customthe solvent was removed under reduced pressure
  4. customto give a residue, which
  5. customafter crystallization from ethyl acetate

Sources & evidence

ORD record
ord-38e4e21a6e9d4a2f8364877d467a7f59
Source dataset
uspto-grants-1981_01
Patent number
US04247697

Reaction notes

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