Hydrochloric Acid → 5-Fluoro-2-hydroxybenzonitrile

HRID 542692Notes

Reaction equation

HRID 542692 reaction equation
[F:1][C:2]1[CH:10]=[C:6]([CH:7]=[N:8]O)[C:5]([OH:11])=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(OC(=O)C)(=O)C.O.C(O)C>[C:7]([C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:11])#[N:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1363350925-Fluorosalicylaldoxime

Product 1

HCID 129192915-Fluoro-2-hydroxybenzonitrileYield 87.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 7918Acetic AnhydrideSolvent

Procedure

5-Fluorosalicylaldoxime (20.2 g, 0.13 mol) was dissolved in acetic anhydride (100 ml), followed by refluxing for 5 hours, distilling off acetic anhydride under reduced pressure after completion of the reaction, adding to the remaining oily material, a solution of KOH (20 g) dissolved in water (100 ml) and ethanol (100 ml), heating the mixture at 80° C. for 2 hours, allowing to cool down to room temperature, adding 6N-hydrochloric acid (50 ml) and water (200 ml) to deposit crystals, filtering the crystals, and recrystallizing from methanol (30 ml) to obtain acicular crystals (15.6 g). M.p. 121°~122° C.

Workup

  1. temperatureby refluxing for 5 hours
  2. distillationdistilling off acetic anhydride under reduced pressure
  3. customafter completion of the reaction
  4. additionadding to the remaining oily material
  5. filtrationfiltering the crystals
  6. customrecrystallizing from methanol (30 ml)

Sources & evidence

ORD record
ord-187e501355324042b6d32f309d786f9c
Source dataset
uspto-grants-1987_04
Patent number
US04659501

Reaction notes

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