p-Toluenesulfonic acid → HCID 178449923, compound

HRID 1531244Notes

Reaction equation

HRID 1531244 reaction equation
[C:1]([NH:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[OH:7][C:8]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:9]=1[CH:10]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[OH:7][C:8]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:9]=1[CH:10]=[N+:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[O-:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 668085-NitrosalicylaldehydeHCID 98586N-tert-butylhydroxylamine

Product 1

HCID 178449923HCID 178449923, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of tert-butylhyroxylamine (10.5 g, 120 mmol), 2-hydroxy-5-nitrobenzaldehyde (15 g, 90 mmol) and p-toluenesulfonic acid (1.6 g, 9 mmol) in benzene (375 mL) was refluxed in a flask fitted with a Dean-Stark trap until no more aldehyde was detectable by TLC. The mixture was cooled and the resulting suspension was filtered. The title compound was isolated in 75.1% yield as a pale yellow solid, m.p. 172° C.

Workup

  1. temperaturewas refluxed in a flask
  2. temperatureThe mixture was cooled
  3. filtrationthe resulting suspension was filtered

Sources & evidence

ORD record
ord-2595f7e95428405f9ec8e0f94f862247
Source dataset
uspto-grants-2001_03
Patent number
US06197826B1

Reaction notes

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