Benzoyl chloride → 2-Phenyl-1,3-benzoxazol-6-ol

HRID 265213Notes

Reaction equation

HRID 265213 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10].[C:11](Cl)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([C:11]2[O:10][C:4]3[CH:5]=[C:6]([OH:7])[CH:8]=[CH:9][C:3]=3[N:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 8358692-Phenyl-1,3-benzoxazol-6-ol

Procedure

0.005 mol of 4-aminoresorcinol hydrochloride were dissolved in 7.5 ml of benzoyl chloride, while heating, and the solution was then boiled under reflux for 7 hours. The excess benzoyl chloride was subsequently distilled off in vacuo, 10 ml of ethanol were added to the residue and the mixture was boiled up briefly and, after cooling, rendered alkaline with 10M NaOH solution. The alkaline solution was introduced into 200 ml of water and brought to pH 3 with concentrated hydrochloric acid, using a pH-meter. The crystal mass which precipitated here was filtered off with suction and recrystallized from 15 ml of toluene. The dried product (250 mg) was uniform according to thin layer chromatography (silica gel plate, ethyl acetate/glacial acetic acid 24:1).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 7 hours
  3. distillationThe excess benzoyl chloride was subsequently distilled off in vacuo, 10 ml of ethanol
  4. additionwere added to the residue
  5. temperatureafter cooling
  6. additionThe alkaline solution was introduced into 200 ml of water
  7. customThe crystal mass which precipitated here
  8. filtrationwas filtered off with suction
  9. customrecrystallized from 15 ml of toluene

Sources & evidence

ORD record
ord-d71bf964be36420dabc0004092665c55
Source dataset
uspto-grants-1997_07
Patent number
US05648229

Reaction notes

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