p-Toluenesulfonic acid → HCID 86586361, compound

HRID 890629Notes

Reaction equation

HRID 890629 reaction equation
[C:1]([C:6]1[C:13]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][C:9]([CH:10]=O)=[CH:8][C:7]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:22]([NH:26][OH:27])([CH3:25])([CH3:24])[CH3:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]([C:6]1[C:13]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][C:9]([CH:10]=[N+:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[O-:27])=[CH:8][C:7]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 98586N-tert-butylhydroxylamineHCID 15550532HCID 15550532, compound

Product 1

HCID 86586361HCID 86586361, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-isobutanoyl-3,5-di-tert-butylbenzaldehyde (7.00 g, 0.023 mol) in benzene (200 mL) was added tert-butylhydroxylamine (2.56 g, 0.029 mol) and p-toluenesulfonic acid (0.100 g). Using a Dean-Stark trap, the resulting mixture was refluxed until no more aldehyde was detected by TLC (Rf=0.30 for product and 0.89 for starting material using 3:1 hexanes/EtOAc). The solvent was removed in vacuo and the residue was thoroughly washed with hexanes. The title compound was isolated in 50.8% yield as a white solid, m.p. 197.1–208.1° C.

Workup

  1. customThe solvent was removed in vacuo
  2. washthe residue was thoroughly washed with hexanes

Sources & evidence

ORD record
ord-b4a6e8b79b044395b01be095f8bbe9f3
Source dataset
uspto-grants-2006_02
Patent number
US06998419B2

Reaction notes

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