p-Toluenesulfonic acid → HCID 86586364, compound

HRID 890632Notes

Reaction equation

HRID 890632 reaction equation
[C:1]([C:7]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:10]([CH:11]=O)=[CH:9][C:8]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:23]([NH:27][OH:28])([CH3:26])([CH3:25])[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]([C:7]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:10]([CH:11]=[N+:27]([C:23]([CH3:26])([CH3:25])[CH3:24])[O-:28])=[CH:9][C:8]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 98586N-tert-butylhydroxylamineHCID 15550539HCID 15550539, compound

Product 1

HCID 86586364HCID 86586364, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-pentanoyl-3,5-di-tert-butylbenzaldehyde (17.48 g, 0.050 mol) in benzene (250 mL) was added tert-butylhydroxylamine (4.57 g, 0.0510 mol) and p-toluenesulfonic acid (0.080 g). Using a Dean-Stark trap, the resulting mixture was refluxed until no more aldehyde was detected by TLC (Rf=0.43 for product using 1:1 hexanes/EtOAc). The solvent was removed in vacuo and the residue was thoroughly washed with hexanes. The title compound was isolated (56.50% yield) as a white solid, m.p. 195.5–204.8° C.

Workup

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

Sources & evidence

ORD record
ord-73ccb4de09c54d1cb1ec8c18acc0577b
Source dataset
uspto-grants-2006_02
Patent number
US06998419B2

Reaction notes

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