HCID 20216272, compound → HCID 20216264, compound

HRID 236569Notes

Reaction equation

HRID 236569 reaction equation
[C:1]([C:3]([OH:29])([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1)#[CH:2].[H][H]>[Pd].C1C=CC=CC=1>[CH2:1]([C:3]([OH:29])([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 20216272HCID 20216272, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20216264HCID 20216264, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

21.7 g. of α-ethinyl-α-(2,4-dichlorophenyl)-4-[3-(dipropylamino)-propoxy]-benzylalcohol are dissolved in 210 ml. of benzene, and the solution is hydrogenated in the presence of 1.1 g. of a 10% palladium-on-charcoal catalyst. When the uptake of the calculated amount of hydrogen is complete (about 3 hours), catalyst is filtered off and benzene is distilled off. The crude product weighing 21 g. is distilled in vacuo, to yield a product boiling at 194° to 196° C./6.6 Pa.

Workup

  1. custom(about 3 hours), catalyst
  2. filtrationis filtered off
  3. distillationbenzene is distilled off
  4. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-9be26211236c4cb2be22f5e8de2a09bf
Source dataset
uspto-grants-1987_02
Patent number
US04645779

Reaction notes

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