Ethanol → 1-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenyl-nitrone

HRID 1287550Notes

Reaction equation

HRID 1287550 reaction equation
[Cl-].[C:2]([C:6]1[CH:7]=[C:8]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[CH2:9][N+:10]1C=CC=C[CH:11]=1)([CH3:5])([CH3:4])[CH3:3].C([OH:26])C.N([C:29]1[CH:34]=[CH:33]C=[CH:31][CH:30]=1)=O.[OH-].[Na+]>O>[C:2]([C:6]1[CH:7]=[C:8]([C:9]2([N+:10]([O-:26])=[CH2:11])[CH:31]=[CH:30][CH:29]=[CH:34][CH2:33]2)[CH:16]=[C:17]([C:20]([CH3:22])([CH3:21])[CH3:23])[C:18]=1[OH:19])([CH3:4])([CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 11473NitrosobenzeneHCID 14798Sodium HydroxideHCID 104969033,5-Di-t-butyl-4-hydroxy-benzylpyridinium chloride

Product 1

HCID 867340661-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenyl-nitroneYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a clean dry 250 ml. round bottom 3-neck flask equipped with a magnetic stirrer, thermometer and addition funnel was added 6.69 g. (0.02 mole) of 3,5-di-t-butyl-4-hydroxy -benzylpyridinium chloride in 100 ml. of ethanol and 2.36 g. (0.022 mole) of nitrosobenzene. The clear solution was cooled to 0° to 5° C. and sodium hydroxide (2.45 g.; 0.06 mole) in 60 ml. of water was added dropwise in 40 minutes. The reaction mixture was stirred an additional 3 hours at ambient temperature and then diluted with 50 ml. water, filtered, and the collected product dried to yield 5.07 g. (79.2% yield) of 1-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenyl-nitrone, MP-137°-140° C.

Workup

  1. customTo a clean dry 250 ml
  2. customround bottom 3-neck flask equipped with a magnetic stirrer
  3. additionthermometer and addition funnel
  4. additionwas added 6.69 g
  5. temperatureThe clear solution was cooled to 0° to 5° C.
  6. additiondiluted with 50 ml
  7. filtrationwater, filtered
  8. customthe collected product dried
  9. customto yield 5.07 g

Sources & evidence

ORD record
ord-10d16d64c529414ca4f2456275f7b285
Source dataset
uspto-grants-1976_10
Patent number
US03985709

Reaction notes

Loading…