p-Toluenesulfonic acid → N-(3-formylphenyl)acetamide

HRID 256182

Reaction equation

HRID 256182 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH:2]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1)=[O:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13987600N-[3-(1,3-dioxolan-2-yl)phenyl]acetamide

Product 1

HCID 256849N-(3-formylphenyl)acetamideYield 100.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-[3-(1,3-dioxolan-2-yl)phenyl]acetamide (50.0 g, 0.24 mole) and p-toluenesulfonic acid (1.0 g) in acetone (750 mL) was stirred at room temperature for 72 hours. The solution was filtered through a pad of neutral alumina and concentrated in vacuo to afford N-(3-formylphenyl)acetamide (39.4 g, 100%), mp 68°-70° C., used without further purification below.

Workup

  1. filtrationThe solution was filtered through a pad of neutral alumina
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a1da0083d5e4beb8dfc71136665e958
Source dataset
uspto-grants-1987_10
Patent number
US04701459

Linked notes

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