Hydrochloric Acid → HCID 53939912, compound

Temperature

40 °C

to a stirred solution of 3-fluorophenol (10.4 g) and potassium hydroxide (85%, 6.1 g) in water (20 ml) at 60° C. was added dropwise over 1 h a solution of 37% aqueous formaldehyde solution (14.3 ml) in added water (20 ml). The mixture was cooled to 40° C., stirred for 18 h then cooled to room temperature and acidified with dilute hydrochloric acid. The mixture was extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed (water, brine), dried (sodium sulfate), concentrated in vacuo and purified by column chromatography (SiO2; ethyl acetate-isohexane, 1:1) to give the product as a white, crystalline solid (1.0 g, 8%): δH (400 MHz, DMSO-d6) 9.70 (1H, m, OH), 7.21 (1H, t, J 8.5 Hz), 6.58 (1H, dd, J 8, 2, Hz), 6.51 (1H, dd, J 12, 2 Hz), 4.98 (1H, m, OH) and 4.41 (2H, s); HPLC (XTERRA, 50/80, 235 nm) 93% (0.54 min).

1. temperaturethen cooled to room temperature
2. extractionThe mixture was extracted with ethyl acetate (2×100 ml)
3. washThe combined organic extracts were washed (water, brine)
4. dry with materialdried (sodium sulfate)
5. concentrationconcentrated in vacuo
6. custompurified by column chromatography (SiO2; ethyl acetate-isohexane, 1:1)

ORD record

ord-dcd8b7e663fd480cbf9a219f021852dc

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07022707B2