Acetic Acid → 3-Fluorosalicylaldehyde

Participants

Reaction Steps

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.

Provenance & Evidence