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

HRID 1448696Notes

Reaction equation

HRID 1448696 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)-2,2,6,6-tetramethylpiperidine (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.

Workup

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

Sources & evidence

ORD record
ord-d07a990d8da24c8f97de34cf2f0b24d3
Source dataset
uspto-grants-1980_02
Patent number
US04187213

Reaction notes

Loading…