反应详情

温度

7 °C

A mixture of 8-hydroxy-1,4-dioxaspiro[4.5]decane (237 g, 1.5 mol) and 700 ml of pyridine was stirred at 0° C. while p-toluenesulfonyl chloride was added portion-wise. After the addition was completed the mixture was stirred for two days at 7° C. The mixture was poured into a 4-kg mixture of equal parts of ice and water with vigorous stirring. After about fifteen minutes a solid separated; this was filtered and washed with water. Dissolved the solid in CH2Cl2 and separated CH2Cl2 solution from residual water. The organic layer was dried (K2CO3 --Na2SO4), filtered and concentrated in vacuo at 36° C. The solution remaining was diluted with Skellysolve B and cooled to -75° C. with stirring. The white solid was filtered and dried in vacuo to give 435 g (92.9%), mp 65°-67.5° C. of the subtitled intermediate. IR C=C (1600), --SO2O-- (1350, 1180), C--O/S--O--C (1105, 945, 925), --SO3 -- (675); nmr (CDCl3) was in accordance with the structure assignment; mass spectrum m/e 312 (M+).

1. additionwas added portion-wise
2. additionAfter the addition
3. customAfter about fifteen minutes a solid separated
4. filtrationthis was filtered
5. washwashed with water
6. dissolutionDissolved the solid in CH2Cl2
7. customseparated CH2Cl2 solution from residual water
8. dry with materialThe organic layer was dried (K2CO3 --Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo at 36° C
11. additionThe solution remaining was diluted with Skellysolve B
12. temperaturecooled to -75° C.
13. stirringwith stirring
14. filtrationThe white solid was filtered
15. customdried in vacuo