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-02721cc0f01345be9e12390ff0c5239e

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420066B2