Formaldehyde → 2-Hydroxy-4-iodobenzaldehyde

To a solution of 3-iodophenol (3.00 g, 13.6 mmol) in acetonitrile (50 mL) was added magnesium chloride (3.89 g, 40.9 mmol), triethylamine (7.6 mL, 55 mmol), and paraformaldehyde (1.64 g, 55 mmol). The reaction mixture was refluxed overnight, then neutralized with saturated aqueous ammonium chloride. The resultant red precipitate was removed by filtration, and the filtrate was extracted with ethyl acetate. The precipitate was dissolved in methanol and added to the combined organic extracts, which were then dried over magnesium sulfate. The solvent was removed under reduced pressure to provide an orange solid (5.4 g) as the crude product. This material was used in the subsequent step without further purification.

1. temperatureThe reaction mixture was refluxed overnight
2. customThe resultant red precipitate was removed by filtration
3. extractionthe filtrate was extracted with ethyl acetate
4. dissolutionThe precipitate was dissolved in methanol
5. additionadded to the combined organic extracts, which
6. dry with materialwere then dried over magnesium sulfate
7. customThe solvent was removed under reduced pressure

ORD record

ord-35bbc710d6b94f938ab960e60f671581

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659412B2