反应详情

A mixture of 1-chloro-4-acetoxynonane (Ex. 1, Step B-3) (35.3 g., 0.16 mole) and sodium iodide (120 g., 0.8 mole) in acetone (350 ml.) is stirred and heated at reflux with exclusion of light for 10 hours. The resulting suspension is filtered and the collected sodium chloride washed with acetone. The combined filtrate and washings are evaporated in vacuo leaving a residual mass which is partitioned between ether and water. The organic extract is washed with dilute aqueous sodium thiosulfate and water, dried over sodium sulfate and evaporated in vacuo providing the title compound as a colorless liquid (48.7 g., 98%), pmr (CDCl3) δ 2.0 (s, 3H), 3.18 (t, 2H) and 4.98 (m, H).

1. temperatureheated
2. temperatureat reflux with exclusion of light for 10 hours
3. filtrationThe resulting suspension is filtered
4. washthe collected sodium chloride washed with acetone
5. customThe combined filtrate and washings are evaporated in vacuo
6. customleaving a residual mass which
7. customis partitioned between ether and water
8. extractionThe organic extract
9. washis washed with dilute aqueous sodium thiosulfate and water
10. dry with materialdried over sodium sulfate
11. customevaporated in vacuo