Sulfuric Acid → 4-(Oxazol-2-yl)phenol

HRID 359830Notes

Reaction equation

HRID 359830 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.N([O-])=[O:14].[Na+].S(=O)(=O)(O)O>>[O:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([OH:14])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 123717394-(1,3-Oxazol-2-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 1356214594-(Oxazol-2-yl)phenolYield 47.9%

Procedure

2-(4-Aminophenyl)oxazole [m.p. 121°-123° C.; Rosenbaum et al., J. Am. Chem. Soc. 64, 2444 (1942)] (10.3 g) was diazotized with 4.93 g of sodium nitrite and 215 ml of 2N sulfuric acid. The resulting diazonium salt was heated until no more nitrogen was evolved, and the product was isolated and recrystallized from ethylene dichloride to give 4.96 g of 4-(2-oxazolyl)phenol, yellow crystals, m.p. 167°-168° C.

Workup

  1. customthe product was isolated
  2. customrecrystallized from ethylene dichloride

Sources & evidence

ORD record
ord-adc061f5305e4c9ea1a9e3c2e5ebf8cb
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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