Diethylene Glycol Monoethyl Ether → 2-Fluoro-4-methylbenzoic acid

Participants

Reaction Steps

Compound of Step 1 (14 g, 105 mmol, 1 eq) was dissolved in 2-(2-ethoxyethoxy) ethanol (105 mL) and KOH (105 ml of a 8 M solution, 840 mmol, 8 eq) was added, the mixture was refluxed under nitrogen for 3 hours. The mixture was cooled and the pH set to 3. The product was extracted with EtOAc and the organic layer was washed 3 times with water and dried with sodium sulfate. The crude mixture was purified on silica using a 0-3% acetic acid/toluene gradient. 3.1 g of the desired compound (19%) was obtained.

Provenance & Evidence