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

HRID 127641Notes

Reaction equation

HRID 127641 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 residue was washed with hot xylene. 2-(4-Hydroxyphenyl)benzoxazole was obtained by crystallization from ethanol in 64% yield (m.p. 253°). A mixture of the sodium salt of 2-(4-hydroxyphenyl)benzoxazole (0.01 mole) and 4-(2-bromoethoxy)-2-hydroxybenzophenone (0.01 mole) in 250 ml of ethanol was refluxed for 20 hours. The reaction mixture was cooled, 200 ml. of water was added and the product, I, was filtered out. Other multichromophoric compounds can be prepared by substitution of other benzoxazoles for 2-(p-hydroxyphenyl)benzoxazole.

Workup

  1. customThe nitrobenzene was removed
  2. washthe residue was washed with hot xylene

Sources & evidence

ORD record
ord-252f41d66ba84710acbf19950f673a04
Source dataset
uspto-grants-1981_03
Patent number
US04256626

Reaction notes

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