N-[4-hydroxy-3,5-di-t-butyl-phenylacetyl]-2-hydroxyaniline → 2-[4-Hydroxy-3,5-di-t-butyl-benzyl]-benzoxazole

HRID 842127Notes

Reaction equation

HRID 842127 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2O)=[O:14])=[CH:4][C:3]=1[C:23]([CH3:26])([CH3:25])[CH3:24]>CCCCCC>[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:9])[CH3:10])=[CH:6][C:5]([CH2:12][C:13]2[O:14][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=2)=[CH:4][C:3]=1[C:23]([CH3:25])([CH3:24])[CH3:26]

Participants

3

Reactant 1

HCID 22618275N-[4-hydroxy-3,5-di-t-butyl-phenylacetyl]-2-hydroxyaniline

Product 1

HCID 226182712-[4-Hydroxy-3,5-di-t-butyl-benzyl]-benzoxazole

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A sample of N-[4-hydroxy-3,5-di-t-butyl-phenyl-acetyl]-2-hydroxyaniline (12.0 g, 0.033 mol) was heated at 260° under nitrogen for 50 minutes. After cooling, the material was heated at reflux with hexane (50 ml) until most of the sample was dissolved. The mixture was filtered while hot and allowed to cool. Filtration afforded 5.4 g (49%) of nearly pure title compound. Pure title compound was obtained after two further crystallizations (with charcoal) from hexane, mp 94-96° C.

Workup

  1. temperatureAfter cooling
  2. temperaturethe material was heated
  3. dissolutionwas dissolved
  4. filtrationThe mixture was filtered while hot and
  5. temperatureto cool
  6. filtrationFiltration

Sources & evidence

ORD record
ord-20c289b24e904353950f1091776eacf3
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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