反应详情

100 ml of benzyl alcohol (0.97 mol) is cooled to 5° in an ice-bath and under a nitrogen atmosphere. 0.32 g of sodium (0.0139 mole; washed with hexane to remove the mineral oil) is slowly added to the rapidly stirred benzyl alcohol. The addition of the sodium is made at such a rate that the temperature remains below 20°. After the addition of the sodium has been completed the mixture is allowed to stir for 1/2 hour and slowly warmed to room temperature. Slowly, and with stirring 20 g of 1,5-hexadiene diepoxide (0.175 mole) is added to the mixture. After the addition of the diepoxide has been completed, the reaction mixture is heated at 150° for 16 hours. The mixture is then cooled to room temperature and with stirring is poured into 350 ml of water. The aqueous mixture is extracted with 2×250 ml portions of chloroform, the CHCl3 extracts are combined and dried over anhydrous sodium sulfate. The CHCl3 is removed in vacuo and the colorless oil vacuum distilled through a 10 cm vigreux distilling column. The fraction distilling at 151°-155° @0.5 mm is collected yielding 18.52 g (48%) of the above compound.

1. washwashed with hexane
2. customto remove the mineral oil)
3. additionis slowly added to the rapidly stirred benzyl alcohol
4. additionThe addition of the sodium
5. customremains below 20°
6. additionAfter the addition of the sodium
7. additionis added to the mixture
8. additionAfter the addition of the diepoxide
9. temperaturethe reaction mixture is heated at 150° for 16 hours
10. temperatureThe mixture is then cooled to room temperature
11. stirringwith stirring
12. extractionThe aqueous mixture is extracted with 2×250 ml portions of chloroform
13. dry with materialdried over anhydrous sodium sulfate
14. customThe CHCl3 is removed in vacuo
15. distillationthe colorless oil vacuum distilled through a 10 cm
16. distillationvigreux distilling column
17. distillationThe fraction distilling at 151°-155° @0.5 mm
18. customis collected