Hydrochloric Acid → HCID 58286932, compound

2-Carboxymethyl-6-fluoro-benzoic acid (11.16 g, 56.32 mmol) in acetic anhydride (65 mL, 690 mmol) was heated at 110° C. for 60 minutes. Pyridine (20 mL, 250 mmol) was added. Gas evolution was observed. The reaction mixture was refluxed overnight and rotovaped. The residue was dissolved in tetrahydrofuran (100 mL) and 4 M aq. NaOH (100 mL) was added. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was acidified with conc. HCl (aq). The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×300 mL). The combined organic phases were washed with brine, dried over MgSO4 and rotavaped. 20 mL toluene was added and the mixture was rotovaped to give crude 2-Fluoro-6-(2-oxo-propyl)-benzoic acid (12.3 g, yield 55.7%, purity ca. 50%). The purity was estimated by 1H NMR and the crude product was used in the next step without further purification.

1. temperatureThe reaction mixture was refluxed overnight
2. customThe two phases were separated
3. extractionthe aqueous phase was extracted with ethyl acetate (2×300 mL)
4. washThe combined organic phases were washed with brine
5. dry with materialdried over MgSO4
6. addition20 mL toluene was added

ORD record

ord-a3098dbb419c49808dd06ec488814009

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415356B2