Water → 1,3,5-Triiodo-2,4,6-tris-(oxiranylmethoxymethyl)benzene

HRID 1271809Notes

Reaction equation

HRID 1271809 reaction equation
[OH-:1].[Na+].[I:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([I:12])[C:7]([CH2:13][OH:14])=[C:6]([I:15])[C:5]=1[CH2:16][OH:17].[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.[OH2:23]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[I:3][C:4]1[C:5]([CH2:16][O:17][CH2:18][CH:20]2[CH2:21][O:22]2)=[C:6]([I:15])[C:7]([CH2:13][O:14][CH2:5][CH:4]2[CH2:9][O:1]2)=[C:8]([I:12])[C:9]=1[CH2:10][O:11][CH2:6][CH:7]1[CH2:8][O:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 206936271,3,5-Triiodo-2,4,6-trihydroxymethylbenzene

Product 1

HCID 184548791,3,5-Triiodo-2,4,6-tris-(oxiranylmethoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

55 ml of a 32% NaOH solution is added in drops at room temperature to a mixture that consists of 11.0 g (20.1 mmol) of 1,3,5-triiodo-2,4,6-trishydroxymethylbenzene, 55.5 g (0.6 mol) of epichlorohydrin and 1.1 g (3.2 mmol) of tetrabutylammonium hydrogen sulfate within 1 hour, and then it is stirred for 12 hours. It is mixed with 150 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-b4c70f6b7b094d908dc42c6df188eb07
Source dataset
uspto-grants-2007_04
Patent number
US07208140B2

Reaction notes

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