Acetone → HCID 67421272, compound

Temperature

55 °C

10 mL of trifluoroacetic anhydride and 4 mL of acetone were added to a slurry of 2,5-dihydroxybenzoic acid (available from Aldrich) (2 g, 13 mmol) in 16 mL of trifluoroacetic acid. The mixture was stirred at 55° C. for 23 h and then at 85° C. for 2.5 h under a nitrogen atmosphere. The reaction mixture was concentrated under vacuum, dissolved and re-concentrated from toluene twice, and dried under vacuum. The crude solid was dissolved in ethyl acetate and washed twice with saturated sodium bicarbonate solution and once with brine. The organic fraction was dried over sodium sulfate and concentrated. Crude product was purified by column chromatography (eluting from silica gel with a gradient of 5 to 50% ethyl acetate in hexanes) to provide the title product as a yellow solid 0.47 g. 1H NMR (200 MHz, CDCl3): δ (ppm)=7.43 (d, J=2.8 Hz, 1H), 7.08 (dd, J=9.0, 3.1 Hz, 1H), 6.85 (d, J=9.0 Hz, 1H), 5.45 (s, 1H), 1.71 (s, 6H).

1. waitat 85° C. for 2.5 h under a nitrogen atmosphere
2. concentrationThe reaction mixture was concentrated under vacuum
3. dissolutiondissolved
4. concentrationre-concentrated from toluene twice
5. customdried under vacuum
6. dissolutionThe crude solid was dissolved in ethyl acetate
7. washwashed twice with saturated sodium bicarbonate solution and once with brine
8. dry with materialThe organic fraction was dried over sodium sulfate
9. concentrationconcentrated
10. customCrude product was purified by column chromatography (
11. washeluting from silica gel with a gradient of 5 to 50% ethyl acetate in hexanes)

ORD record

ord-9ee754e4518646a39ab7a0304b431009

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149476B2