Hydrochloric Acid → 1-Iodo-4-octylbenzene

Temperature

0 °C

To a suspension of 4-octylaniline (80.0 g, 389.6 mmol) in water (780 mL) was added aqueous HCl (40 mL) at room temperature. After the mixture was cooled to 0° C., more aqueous HCl (43 mL) was added, followed by dropwise addition of a solution of NaNO2 (26.9 g, 389.6 mmol) in water (195 mL). To the resulting arenediazonium salt solution was added dropwise a solution of potassium iodide (64.67 g, 389.6 mmol) in water (195 mL). The resulting mixture was heated with stirring at 40° C. After two hours, sodium thiosulfate was added to decolorize and the product was extracted with ether. The ethereal extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a crude oil. The crude material was dissolved in ether and filtered through a plug of silica gel three times and dried in vacuo to give 1-iodo-4-octylbenzene as a colorless oil. The product was used in the next step without further purification.

1. temperatureThe resulting mixture was heated
2. extractionthe product was extracted with ether
3. extractionThe ethereal extract
4. washwas washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo
7. customto give a crude oil
8. filtrationfiltered through a plug of silica gel three times
9. customdried in vacuo

ORD record

ord-1f1013ac3331462c969c553ef7c27cc5

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902363B2