Acetic Acid → 2-(Decane-1-sulfonyl)butanedioic acid

HRID 1084295Notes

Reaction equation

HRID 1084295 reaction equation
C(O)(=[O:3])C.[CH2:5]([S:15][CH:16]([CH2:20][C:21]([OH:23])=[O:22])[C:17]([OH:19])=[O:18])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].OO.[OH2:26]>>[CH2:5]([S:15]([CH:16]([CH2:20][C:21]([OH:23])=[O:22])[C:17]([OH:19])=[O:18])(=[O:3])=[O:26])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 2830369Butanedioic acid, (decylthio)-

Product 1

HCID 157090172-(Decane-1-sulfonyl)butanedioic acid

Procedure

In a 400 ml beaker equipped with a heating mantle, alcohol thermometer, 50 ml dropping funnel, and a stirrer, 100 ml of glacial acetic acid was heated to about 50° C. To this was added 101.32 g of the dry solid C10H21SCH(COOH)CH2COOH.12H2O described above, with stirring and heating to obtain a thick white slurry. Via the dropping funnel, 22.64 ml of 70% H2O2 was then added over a period of 114 minutes at 45°-53° C., resulting in an exothermic reaction. Agitation was then continued for 31/2 hours at 47°-53° C. The resulting homogeneous solution was diluted with 50 ml of water and then cooled to ambient temperature, becoming a thick white slurry which was then held overnight. The slurry was cooled to 5°-10° C., and the solids were collected by filtration. The solids were dissolved in 515 ml of ethyl acetate. This solution was filtered to remove a small amount of insoluble material, washed with three 200 ml portions of water and transferred to a 4,000 ml beaker. Enough ethylacetate was then boiled off to reduce the solution volume to about 300 ml. Heating was discontinued, and with agitation, 1,500 ml of petroleum ether was added via a dropping funnel, resulting in the precipitation of a white solid product. The slurry was cooled to 5°-10° C., and the solids were recovered by filtration. The solids were washed by reslurrying in petroleum ether, again recovered by filtration, and dried overnight at ambient temperature. The resulting product weighed 34.63 g, and NMR analysis in DMSO-D6 showed that it was n-decylsulfonylsuccinic acid, C10H21SO2CH(COOH)CH2COOH. Water was not present at detectable levels, and the only detectable impurity was about 0.2% of fumaric acid. The yield was 53.7% of the theoretical amount, based upon the amount of the sulfide used.

Workup

  1. temperatureheating
  2. customto obtain a thick white slurry
  3. customresulting in an exothermic reaction
  4. custom2 hours
  5. customat 47°-53° C
  6. temperatureThe slurry was cooled to 5°-10° C.
  7. filtrationthe solids were collected by filtration
  8. dissolutionThe solids were dissolved in 515 ml of ethyl acetate
  9. filtrationThis solution was filtered
  10. customto remove a small amount of insoluble material
  11. washwashed with three 200 ml portions of water
  12. temperatureHeating
  13. additionwith agitation, 1,500 ml of petroleum ether was added via a dropping funnel
  14. customresulting in the precipitation of a white solid product
  15. temperatureThe slurry was cooled to 5°-10° C.
  16. filtrationthe solids were recovered by filtration
  17. washThe solids were washed
  18. filtrationagain recovered by filtration
  19. customdried overnight at ambient temperature

Sources & evidence

ORD record
ord-9df3b919bcab4694b115befbc458765f
Source dataset
uspto-grants-1991_04
Patent number
US05004558

Reaction notes

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