Water → 4-Acetyl-2-hydroxybenzonitrile

HRID 480097Notes

Reaction equation

HRID 480097 reaction equation
C([C:4]1[CH:12]=[C:8]([C:9]([NH2:11])=O)[C:7]([OH:13])=[CH:6][CH:5]=1)(=O)C.O=C(Cl)OC(Cl)(Cl)Cl.O.[O:23]1CCO[CH2:25][CH2:24]1>>[OH:13][C:7]1[CH:6]=[C:5]([C:24](=[O:23])[CH3:25])[CH:4]=[CH:12][C:8]=1[C:9]#[N:11]

Participants

5

Reactant 4

HCID 962WaterHCID 10426DiphosgeneHCID 312751,4-DioxaneHCID 1982125-Acetylsalicylamide

Product 1

HCID 187688364-Acetyl-2-hydroxybenzonitrile

Procedure

5-acetylsalicylamide (10.04 g, 56 mmol) and diphosgene (18.4 g, 93 mmol) were heated in dioxane (65 ml) to70° C. under nitrogen for 18 hours. The mixture was cooled, cautiously poured into cold water (700 ml) and stirred for 1 hour to destroy excess diphosgene reagent. The mixture was extracted with ethyl acetate, and the organic solution washed with water and brine, dried over sodium sulfate, filtered, and evaporated. The residue was recrystallized from toluene/acetonitrile to give the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. customto destroy excess diphosgene reagent
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic solution washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized from toluene/acetonitrile

Sources & evidence

ORD record
ord-48abb30d71154eea8c58477658514c87
Source dataset
uspto-grants-2003_11
Patent number
US06649636B1

Reaction notes

Loading…