Formamide → 2,6-Di-tert-butyl-4-(5-methyl-1,3-oxazol-4-yl)phenol

HRID 980331Notes

Reaction equation

HRID 980331 reaction equation
[CH:1]([NH2:3])=[O:2].Br[CH:5]([CH3:23])[C:6]([C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=1)=O>O>[C:19]([C:10]1[CH:9]=[C:8]([C:6]2[N:3]=[CH:1][O:2][C:5]=2[CH3:23])[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]=1[OH:18])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 713FormamideHCID 13173168HCID 13173168, compound

Product 1

HCID 131070192,6-Di-tert-butyl-4-(5-methyl-1,3-oxazol-4-yl)phenolYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4.5 g of formamide and 2.25 g of 4-(2-bromopropionyl)-2,6-di-tert-butylphenol was heated to 150° C. for 1.5 hours. The reaction mixture was poured into water after cooling and then extracted twice each time with 30 ml of toluene. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure and the residue was recrystallized from aqueous methanol to provide 1.1 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyloxazole.

Workup

  1. temperatureafter cooling
  2. extractionextracted twice each time with 30 ml of toluene
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-4a382c7c00ac4e3ab329a75968f8ded3
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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