Sodium Iodide → 3-(2,2-Diethoxy-ethoxy)-benzoic acid ethyl ester

Temperature

120 °C

2-Bromoacetaldehyde diethyl acetal (3 ml, 20 mmol), ethyl-3-hydroxy-benzoate (1.66 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol) and sodium iodide (0.298 g, 2 mmol) were heated at 120° C. in dimethyl formamide (DMF) (15 ml) for 17 hrs. Another batch of 2-bromoacetaldehyde diethyl acetal (3 ml, 20 mmol) was added and the reaction mixture was heated at 120° C. for another 24 hrs. The reaction was cooled to room temperature and all the solvents were evaporated under reduced pressure. The residues were partitioned between dichloromethane (DCM) (200 ml) and water (200 ml). The DCM layer was separated and the aqueous layer was back-extracted with DCM (2×100 ml). All the DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by a column chromatography (4×20 cm). The product was eluted with 100% DCM and the title compound was obtained as a colourless oil (2.21 g, 78.3%).

1. temperatureThe reaction was cooled to room temperature
2. customall the solvents were evaporated under reduced pressure
3. customThe residues were partitioned between dichloromethane (DCM) (200 ml) and water (200 ml)
4. customThe DCM layer was separated
5. extractionthe aqueous layer was back-extracted with DCM (2×100 ml)
6. dry with materialdried over MgSO4
7. customevaporated under reduced pressure
8. customThe residue was purified by a column chromatography (4×20 cm)
9. washThe product was eluted with 100% DCM

ORD record

ord-b64fedd94b484b59b2e7e9b4e20b9624

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09410199B2