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

HRID 462025Notes

Reaction equation

HRID 462025 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[N+](C1C=CC=CC=1)([O-])=O>>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:14]1[C:13]1[CH:16]=[CH:17][C:10]([OH:9])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 58012-AminophenolHCID 7416Nitrobenzene

Product 1

HCID 27855874-(Benzo[d]oxazol-2-yl)phenolYield 73%

Procedure

A mixture containing 5.45 g. (0.05 mole) of o-aminophenol and 6.10 g. (0.05 mole) of p-hydroxybenzaldehyde in 75 ml. of nitrobenzene was heated to reflux for 5 hr. On cooling to 30° a dark solid appears which was filtered, washed with hot toluene, and air-dried. Recrystallization from ethanol gave a 73% yield of 4-(2-benzoxazolyl)phenol (mp 255°-258°).

Workup

  1. additionA mixture containing 5.45 g
  2. temperatureto reflux for 5 hr
  3. temperatureOn cooling to 30° a dark solid appears which
  4. filtrationwas filtered
  5. washwashed with hot toluene
  6. customair-dried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-3527316307514d1eb4762853e64f0e7f
Source dataset
uspto-grants-1977_12
Patent number
US04065427

Reaction notes

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