反应详情

50 g of H(CF2)4CH2OH was dissolved in 100 ml of dimethyl sulfoxide (DMSO). 22.4 g of sodium hydroxide was added with stirring, and then 33 g of allyl chloride was dded slowly at room temperature over 2 hours. Stirring was continued for 5 hours. After filtration of precipitates, the solution was heated on a water bath to remove unreacted allyl chloride. The solution was poured into a large amount of water to separate H(CF2)4CH2OCH2 --CH=CH2. A small quantity of BPO of the order of mg was added to H(CF2)4CH2OCH2 --CH=CH2, and then thiolacetic acid was added with stirring at room temperature over 2 hours. Unreacted thiolacetic acid was removed under reduced pressure. 100 cc of methanol and 10 g of sodium hydroxide were added, and reaction was carried out at 60° C. for 3 hours. After cooling to room temperature, the reaction product was poured into a large amount of water to give crude H(CF2)4CH2OCH2CH2CH2SH. Upon distillation, there was obtained a purified product having bp. 57° C./3 mmHg. The structure of this compound was confirmed by 1H--NMR.

1. stirringStirring
2. filtrationAfter filtration
3. customof precipitates
4. temperaturethe solution was heated on a water bath
5. customto remove unreacted allyl chloride
6. additionThe solution was poured into a large amount of water
7. customto separate H(CF2)4CH2OCH2 --CH=CH2
8. additionA small quantity of BPO of the order of mg was added to H(CF2)4CH2OCH2 --CH=CH2
9. additionthiolacetic acid was added
10. stirringwith stirring at room temperature over 2 hours
11. customwas removed under reduced pressure
12. addition100 cc of methanol and 10 g of sodium hydroxide were added
13. customreaction
14. waitwas carried out at 60° C. for 3 hours