Trifluoroacetic acid → Sodium 4-(nonanoyloxy)benzenesulfonate

HRID 1279904Notes

Reaction equation

HRID 1279904 reaction equation
[C:1]([OH:11])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH:12]1[CH:17]=[C:16](O)[C:15]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:14][CH:13]=1.[Na+:23].C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>>[C:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:14][CH:13]=1)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Na+:23]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8158Nonanoic AcidHCID 9845Trifluoroacetic anhydrideHCID 23674503Sodium o-phenolsulfonate

Product 1

HCID 23673620Sodium 4-(nonanoyloxy)benzenesulfonateYield 94%

Procedure

A 300 ml, round-bottom flask with a nitrogen inlet and a magnetic stir bar was flushed with nitrogen for ten minutes. Nonanoic acid (4.45 g, 28.0 millimoles—mmol), sodium phenolsulfonate (5.00 g, 25.0 mmol) and TFA were placed in the flask which was sealed with a septum cap and the resulting slurry was stirred while being cooled by an ice-water bath. A single rapid addition of TFAA (6.5 ml) was made via syringe. Within one minute the slurry is dissolved to yield a homogeneous solution. The stirring was continued for five minutes. The volatiles were removed by rotary evaporation yielding a white solid that was washed with 100 ml of acetone and collected on a Buchner funnel. The resulting white solid was dried under reduced pressure yielding 7.90 g (94% yield) of sodium 4-(nonanoyloxy)benzene-sulfonate (NOBS). 1H and 13C NMR show complete conversion of the SPS to NOBS.

Workup

  1. customA 300 ml, round-bottom flask with a nitrogen inlet and a magnetic stir bar was flushed with nitrogen for ten minutes
  2. customwas sealed with a septum
  3. customcap
  4. temperaturewhile being cooled by an ice-water bath
  5. customwas made via syringe
  6. dissolutionWithin one minute the slurry is dissolved
  7. customto yield a homogeneous solution
  8. customThe volatiles were removed by rotary evaporation
  9. customyielding a white solid
  10. washthat was washed with 100 ml of acetone
  11. customcollected on a Buchner funnel
  12. customThe resulting white solid was dried under reduced pressure

Sources & evidence

ORD record
ord-3eec095a9bbf472fa0fcc6121990c927
Source dataset
uspto-grants-2002_09
Patent number
US06448430B1

Reaction notes

Loading…