3-(4-aminophenyl)-1-(4-methylphenyl)propan-1-one → 3-(4-aminophenyl)-1-(4-methylphenyl)propan-1-ol

HRID 1285278Notes

Reaction equation

HRID 1285278 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[H][H]>O1CCCC1.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:18])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 27682673-(4-aminophenyl)-1-(4-methylphenyl)propan-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 43137463-(4-aminophenyl)-1-(4-methylphenyl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

60 g of the 1-(4-methylphenyl)-3-(4-aminophenyl)-n-propan-1-one prepared as described in Example A were hydrogenated, in 1 liter of tetrahydrofuran, in the presence of 5 g of 10% strength Pd on charcoal, under 1.1 bar, until 5.5 liters of hydrogen had been absorbed. The catalyst was separated off and the reaction solution was evaporated down, and the oil obtained crystallized on trituration with diisopropyl ether. After the white crystals had been dried, 53 g (88% of theory) of the carbinol of melting point 63°-65° C. were obtained.

Workup

  1. customhad been absorbed
  2. customThe catalyst was separated off
  3. customthe reaction solution was evaporated down
  4. customthe oil obtained
  5. customcrystallized on trituration with diisopropyl ether
  6. customAfter the white crystals had been dried
  7. custom53 g (88% of theory) of the carbinol of melting point 63°-65° C. were obtained

Sources & evidence

ORD record
ord-16f89062146b4684aa3f9195002e85bc
Source dataset
uspto-grants-1986_01
Patent number
US04566900

Reaction notes

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