Water → 1,3,5-Triiodo-2,4,6-tris-(toluenesulfonyloxy)methylbenzene

HRID 1271811Notes

Reaction equation

HRID 1271811 reaction equation
[C:1]1([CH3:11])[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[I:12][C:13]1[C:18]([CH2:19][OH:20])=[C:17]([I:21])[C:16]([CH2:22][OH:23])=[C:15]([I:24])[C:14]=1[CH2:25][OH:26].[OH2:27]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1(C)C=CC=CC=1>[I:12][C:13]1[C:14]([CH2:25][O:26][S:7]([C:2]2[C:1]([CH3:11])=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:9])=[O:8])=[C:15]([I:24])[C:16]([CH2:22][O:23][S:7]([C:2]2[C:1]([CH3:11])=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:27])=[C:17]([I:21])[C:18]=1[CH2:19][O:20][S:7]([C:2]1[C:1]([CH3:11])=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:9])=[O:8]

Participants

7

Reactant 3

HCID 962WaterHCID 8623o-Toluenesulfonyl chlorideHCID 206936271,3,5-Triiodo-2,4,6-trihydroxymethylbenzene

Product 1

HCID 1317263391,3,5-Triiodo-2,4,6-tris-(toluenesulfonyloxy)methylbenzene

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

76.3 g (400 mmol) of toluenesulfonic acid chloride is added in drops to a mixture that consists of 50.0 g (91.4 mmol) of 1,3,5-triiodo-2,4,6-tris-hydroxymethylbenzene and 3 g (8.7 mmol) of tetrabutylammonium hydrogen sulfate in 200 ml of 32% NaOH solution and 300 ml of toluene at room temperature, and then it is stirred for 12 hours. It is mixed with 300 ml of water and extracted twice with 200 ml each of toluene. The combined organic phases are dried on sodium sulfate, the solvent is evaporated to the dry state and chromatographed on silica gel (mobile solvent:hexane/ethyl acetate 10:1). The fractions that contain the product are combined and concentrated by evaporation.

Workup

  1. extractionextracted twice with 200 ml each of toluene
  2. customThe combined organic phases are dried on sodium sulfate
  3. customthe solvent is evaporated to the dry state
  4. customchromatographed on silica gel (mobile solvent:hexane/ethyl acetate 10:1)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0f28f603db604c1e8fcb576f8eaace0e
Source dataset
uspto-grants-2007_04
Patent number
US07208140B2

Reaction notes

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