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

HRID 1764184Notes

Reaction equation

HRID 1764184 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 5 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-320131ce11cf48a6b601d1361b132d5a
Source dataset
uspto-grants-1978_09
Patent number
US04115348

Reaction notes

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