Reaction #445535

Reaction equation

8-hydroxy-1,4-dioxaspiro[4.5]decane

pyridine

p-toluenesulfonyl chloride

→

subtitled intermediate

8-Tosyloxy-1,4-dioxaspiro[4.5]decane

Solvents

water

Conditions

Workup

1. 1
   workup.ADDITIONwas added portion-wise
2. 2
   workup.ADDITIONAfter the addition
3. 3
   OtherAfter about fifteen minutes a solid separated
4. 4
   Filtrationthis was filtered
5. 5
   Washwashed with water
6. 6
   workup.DISSOLUTIONDissolved the solid in CH2Cl2
7. 7
   Otherseparated CH2Cl2 solution from residual water
8. 8
   DryingThe organic layer was dried (K2CO3 --Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated in vacuo at 36° C
11. 11
    workup.ADDITIONThe solution remaining was diluted with Skellysolve B
12. 12
    Temperaturecooled to -75° C.
13. 13
    workup.STIRRINGwith stirring
14. 14
    FiltrationThe white solid was filtered
15. 15
    Otherdried in vacuo

Procedure

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+).

Source