Potassium Iodide → HCID 67059833, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-[(3S)-3,7-dimethyl-6-octenyl]aniline (10.0 g, 43.2 mmol, Example 4) in concentrated HCl (9 mL) and water (100 mL) was cooled to 0° C. and then a solution of sodium nitrate (NaNO2, 2.96 g, 43.2 mmol) in water (22 mL) was added dropwise. To the resulting arenediazonium salt a solution of potassium iodide (7.11 g, 43.2 mmol) in water (22 mL) was added dropwise and the mixture was heated at 40° C. for 2 hours. Sodium thiosulfate was added and the suspension was extracted with ether (3×50 mL) and the combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a dark oil. The crude material was dissolved in ether and filtered through a plug of silica gel to give 1-iodo-4-[(3S)-3,7-dimethyl-6-octenyl]benzene as a colorless oil (9.27 g, 27.1 mmol, 62.5% yield).

Provenance & Evidence