4-Hydroxybenzaldehyde → 4-(Benzo[d]oxazol-2-yl)phenol

HRID 46711Notes

Reaction equation

HRID 46711 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1O>[N+](C1C=CC=CC=1)([O-])=O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[O:7][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 58012-Aminophenol

Product 1

HCID 27855874-(Benzo[d]oxazol-2-yl)phenolYield 64%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Equal molar quantities of p-hydroxybenzaldehyde and o-aminophenol in excess nitrobenzene was refluxed for five hours. The nitrobenzene was removed and the product extracted from the residue with xylene. 2-(4-Hydroxyphenyl)benzoxazole, m.p. 253°, was isolated in 64% yield.

Workup

  1. customThe nitrobenzene was removed
  2. extractionthe product extracted from the residue with xylene

Sources & evidence

ORD record
ord-97774185b32e4ed8a98473624a78a661
Source dataset
uspto-grants-1979_11
Patent number
US04174321

Reaction notes

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