Water → 1-(3-Aminophenyl)ethanol

HRID 2397352Notes

Reaction equation

HRID 2397352 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.[OH-].[K+]>[Pd].P(=O)(O)(O)O>[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 3

HCID 962WaterHCID 8494m-NitroacetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 2224611-(3-Aminophenyl)ethanolYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1004Phosphoric AcidSolvent

Procedure

m-Nitroacetophenone (82.3 g., 0.50 mole), water containing 0.85 mole of phosphoric acid (300 ml.), and 5% palladium on carbon (1.5 g.) were charged and hydrogenated as in Example II. The resulting hydrogenate was neutralized with 45% potassium hydroxide (1.70 mole) and stirred in a cooling bath until precipitation of solids was complete. m-Amino-α-methylbenzyl alcohol was obtained in 86% yield and contained 97.8% pure product with 2.2% m-ethylaniline.

Sources & evidence

ORD record
ord-88e5daa825404dd2ba7892603e4a7729
Source dataset
uspto-grants-1977_05
Patent number
US04021487

Reaction notes

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