Sulfuric Acid → 1-(o-Aminophenyl)-4-hydroxy-1-butanone

HRID 365968Notes

Reaction equation

HRID 365968 reaction equation
[CH:1]1([C:4]([C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2[NH:8]S(C2C=CC(C)=CC=2)(=O)=O)=[O:5])[CH2:3][CH2:2]1.S(=O)(=O)(O)[OH:24].[OH-].[NH4+]>>[NH2:8][C:7]1[CH:19]=[CH:20][CH:21]=[CH:22][C:6]=1[C:4](=[O:5])[CH2:1][CH2:2][CH2:3][OH:24]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 232932452'-(Cyclopropylcarbonyl)-p-toluenesulfonanilide

Product 1

HCID 112061181-(o-Aminophenyl)-4-hydroxy-1-butanoneYield 80%

Conditions

Temperature
90 °C

Procedure

The product of example 2 (1.5 g, 4.7 mmol) is treated with 96% sulfuric acid and heated to 90° C. for 15 minutes. The solution is cooled, adjusted to pH 9 with ammonium hydroxide and extracted with methylene chloride. The combined extracts are concentrated in vacuo to provide 1-(o-aminophenyl)-4-hydroxy-1-butanone (80% yield, mp 58-61° C.). The product is identified by NMR and MS analyses.

Workup

  1. temperatureThe solution is cooled
  2. extractionextracted with methylene chloride
  3. concentrationThe combined extracts are concentrated in vacuo

Sources & evidence

ORD record
ord-8c713a6fd62f4a74b4bcfd81d73ab546
Source dataset
uspto-grants-2000_10
Patent number
US06127576

Reaction notes

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