Hydrochloric Acid → 2-Chloro-4-hydroxybenzaldehyde

3-Chlorophenol (CAS 108-43-0) (49.2 g, 0.380 mol), calcium hydroxide (122.0 g), and sodium carbonate (139.4 g) were suspended in water (872 mL). Chloroform (90.6 g, 0.760 mol) was added for 80 min, and the mixture was refluxed under vigorous stirring for 3 h. The reaction mixture was cooled on ice bath. Concentrated HCl (385 mL) and chloroform (300 mL) were added. The aqueous layer was discarded. The organic one was dried with anhydrous Na2SO4 (50 g) and evaporated in vacuo. The residue was purified by chromatography (silica gel 63-100 μm, 600 g, CCl4→CHCl3→CHCl3/EtOAc 93:7). Fractions containing the product were combined, evaporated, and coevaporated with dioxane to give the title compound (9.77 g, 0.062 mol, 16%) as a white powder. 1H NMR data (DMSO-d6): 11.06 (s, 1H, COH); 10.14 (s, 1H, OH); 7.75 (d, 1H, J=8.5 Hz, Ar—H); 6.92 (d, 1H, J=2 Hz, Ar—H); 6.85 (d.d., 1H, J1=8.5 Hz, J2=2 Hz, Ar—H).

1. temperaturethe mixture was refluxed
2. temperatureThe reaction mixture was cooled on ice bath
3. dry with materialThe organic one was dried with anhydrous Na2SO4 (50 g)
4. customevaporated in vacuo
5. customThe residue was purified by chromatography (silica gel 63-100 μm, 600 g, CCl4→CHCl3→CHCl3/EtOAc 93:7)
6. additionFractions containing the product
7. customevaporated

ORD record

ord-48b7e7731e8b4da5bd0e3af3ae0f8d50

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812040B2