Acetic Acid → 3-Fluorosalicylaldehyde

HRID 1703510Notes

Reaction equation

HRID 1703510 reaction equation
C([C:4]1[C:5]([F:11])=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)=CC.[I-].[K+].O=[O+][O-].O=O.O=O.O=[O+][O-].[I-].II.[C:27](O)(=[O:29])C>O>[F:11][C:5]1[CH:4]=[CH:9][CH:8]=[C:7]([CH:27]=[O:29])[C:6]=1[OH:10]

Participants

10

Reactant 8

HCID 176Acetic AcidHCID 807IodineHCID 977OxygenHCID 4875Potassium Iodide2×HCID 24823Ozone3×HCID 30165Iodide IonHCID 54541314HCID 54541314, compoundHCID 131711318Oxygen ozone

Product 1

HCID 5877883-FluorosalicylaldehydeYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To effect the desired ozonolysis, 87 grams of the propenyl-o-fluorophenol which was prepared above along with 600 grams of glacial acetic acid and 75 grams of water were placed in a 1 liter round bottom flask equipped with a mechanical stirrer, thermometer, gas inlet through a sintered glass sparger and a gas outlet leading to a scrubber containing 400 cc of 2% potassium iodide solution and then to a wet test gas meter. The contents of the flask were cooled to 0° C. under a nitrogen blanket following which an ozone-oxygen gas stream was passed into the stirred reactants at a rate of 8 cubic feet per hour. The stream was generated by passing oxygen through an ozonator so that the stream contained 1.2% ozone. After a period of 5.5 hours, the scrubber containing the potassium iodide solution turned dark due to the ozone oxidation of iodide to iodine thus indicating that the reactants were no longer absorbing ozone. The ozonized solution was transferred to a liquid/liquid extractor containing 1200 cc of water and was extracted for a period of 16 hours with 2.5 liters of benzene. Upon completion of the extraction, the aqueous phase was discarded and the organic phase was washed with a total of 2 liters of benzene. The organic phase was then washed with a total of 2 liters of water which had been saturated with sodium chloride in order to remove the acetic acid and then with 250 cc of a 4% aqueous sodium bicarbonate solution which was also saturated with sodium chloride. The benzene was evaporated on a rotary evaporator to give 70 grams of crude 3-fluorosalicylaldehyde.

Workup

  1. customwere placed in a 1 liter round bottom flask
  2. customequipped with a mechanical stirrer
  3. customthermometer, gas inlet through a sintered glass sparger and a gas outlet leading to a scrubber
  4. extractionwas extracted for a period of 16 hours with 2.5 liters of benzene
  5. extractionUpon completion of the extraction
  6. washthe organic phase was washed with a total of 2 liters of benzene
  7. washThe organic phase was then washed with a total of 2 liters of water which
  8. customto remove the acetic acid
  9. customThe benzene was evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-b3d1bdc98f194268b152a6cec4bdeb96
Source dataset
uspto-grants-1978_11
Patent number
US04124643

Reaction notes

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