Water → 1-(3-Aminophenyl)ethanol

HRID 2397353Notes

Reaction equation

HRID 2397353 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.[H][H].[OH-].[K+]>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:10]([OH:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8494m-NitroacetophenoneHCID 14797Potassium HydroxideHCID 178418361HCID 178418361, compound

Product 1

HCID 2224611-(3-Aminophenyl)ethanolYield 75%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

m-Nitroacetophenone (66.0 g., 0.40 mole), water containing 0.70 mole phosphoric acid (300 ml.), and 5% palladium on carbon (2.0 g.) were hydrogenated as in Example II until hydrogen absorption ceased (2 hours). Work-up after neutralization with 1.40 moles potassium hydroxide gave m-amino-α-methylbenzyl alcohol in 75% yield which was 99% pure by GLC and contained 0.8% m-ethylaniline.

Workup

  1. custom(2 hours)

Sources & evidence

ORD record
ord-34803fe49ce143cc9add29047dd2a79a
Source dataset
uspto-grants-1977_05
Patent number
US04021487

Reaction notes

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