Sulfuric Acid → HCID 14100447, compound

HRID 1165269Notes

Reaction equation

HRID 1165269 reaction equation
S(=O)(=O)(O)O.OS(O)(=O)=O.O=S(=O)=O.[Cl:15][C:16]([Cl:44])([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([Cl:43])([Cl:42])[C:36]([O:38]C(C)C)=[O:37])[C:17]([O:19]C(C)C)=[O:18]>>[Cl:15][C:16]([Cl:44])([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([Cl:42])([Cl:43])[C:36]([OH:38])=[O:37])[C:17]([OH:19])=[O:18]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24681Fuming sulfuric acidHCID 14100446HCID 14100446, compound

Product 1

HCID 14100447HCID 14100447, compoundYield 90%

Conditions

Temperature
3 °C

Procedure

3 g. of a mixture of 96-98% sulphuric acid and oleum (1:1 w/w) cooled to 3° C. are added dropwise to the dry diisopropyl 2,2,15,15-tetrachlorohexadecane-1,16-dioate. The mixture is stirred for 10 minutes at 3° C., a colour change to orange thereby taking place. A further 2 g. of the acid mixture are added dropwise until the ester has completely dissolved and then stirred for 15 minutes at 3° C. The solution is cooled to -78° C. and a mixture of ice/dichloromethane added thereto. The frozen mixture is dissolved by slowly warming to ambient temperature while stirring with a porcelain spatula, the solution thereby becoming colourless. After separation of the phases, the aqueous phase is extracted with dichloromethane and the combined organic extracts are dried over anhydrous sodium sulphate. After removal of the solvent, there are obtained 150 mg. (yield 90% of theory) of a colourless solid; m.p. 113.5°-114.5° C., after recrystallisation from cyclohexane.

Workup

  1. dissolutionhas completely dissolved
  2. stirringstirred for 15 minutes at 3° C
  3. temperatureThe solution is cooled to -78° C.
  4. additionadded
  5. dissolutionThe frozen mixture is dissolved
  6. temperatureby slowly warming to ambient temperature
  7. stirringwhile stirring with a porcelain spatula
  8. customAfter separation of the phases
  9. extractionthe aqueous phase is extracted with dichloromethane
  10. dry with materialthe combined organic extracts are dried over anhydrous sodium sulphate
  11. customAfter removal of the solvent, there
  12. customare obtained 150 mg
  13. customm.p. 113.5°-114.5° C., after recrystallisation from cyclohexane

Sources & evidence

ORD record
ord-92cd410cb5fb45838f2e0989bca54c17
Source dataset
uspto-grants-1990_03
Patent number
US04908385

Reaction notes

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