Ethanol → Ethyl 4-iodobenzoate

To a suspension of 24.9 g (100.4 mmol) of 4-iodobenzoic acid in 46.25 g (58.9 mL, 1.0 mol) of ethanol was added 3 mL of c. sulfuric acid. The resulting mixture was refluxed for 60 minutes, distilled until a clear, homogeneous solution was obtained and then allowed to cool to room temperature. The reaction mixture was extracted and partitioned between pentane (250 mL) and water (250 mL) and the layers were separated. The aqueous phase was washed with 3×100 mL-portions of pentane. All organic phases were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to a dark yellow oil. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a clear, light yellow oil. PMR (CDCl3): δ 1.39 (3H, t, J=7.2 Hz), 4.37 (2H, q, J=7.2 Hz), 7.73-7.82 (4H, m).

1. additionwas added 3 mL of c
2. temperatureThe resulting mixture was refluxed for 60 minutes
3. distillationdistilled until a clear, homogeneous solution
4. customwas obtained
5. extractionThe reaction mixture was extracted
6. custompartitioned between pentane (250 mL) and water (250 mL)
7. customthe layers were separated
8. washThe aqueous phase was washed with 3×100 mL-portions of pentane
9. washwashed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo to a dark yellow oil
13. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

ORD record

ord-49cff47b489e42fe89d473282fbd3bff

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06660755B2