Sodium Iodide → HCID 131729476, compound

HRID 1645411Notes

Reaction equation

HRID 1645411 reaction equation
[CH2:1]1[S:9](=[O:11])(=[O:10])[O:8][CH2:7][CH2:6][O:5][S:2]1(=[O:4])=[O:3].[H-].[Na+].Cl[CH2:15][C:16]1[C:25]2[C:20](=CC=C[CH:24]=2)[CH:19]=[CH:18][CH:17]=1.[Na+].[I-].[CH2:28]([CH2:31]OC)OC>>[CH:24]1[C:25]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:6][C:7]=1[O:8][S:9]([CH:1]([S:2]([OH:5])(=[O:4])=[O:3])[CH3:28])(=[O:11])=[O:10].[CH2:28]=[CH2:31]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 68451-ChloromethylnaphthaleneHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 57513Cyclodisone

Product 1

HCID 131729476HCID 131729476, compoundYield 86%

Procedure

To a solution of 3.5 g of ethylene methanedisulfonate in 60 mL of glyme and 0.9 g of NaH was added 3.4 g of 1-chloromethylnaphthalene followed by 2.6 g of NaI. The solution was stirred overnight and the glyme removed by the rotary evaporator at 20 mm pressure. The residue was taken up in an acid solution and CH2Cl2. The CH2Cl2 was rinsed with a NaHSO3 solution, dried, concentrated, and cyclohexane was added to give 3.9 g (86%) of ethylene 2-naphthyl-1,1-ethanedisulfonate, m.p. 179-183° C. (94-2).

Workup

  1. customthe glyme removed by the rotary evaporator at 20 mm pressure
  2. washThe CH2Cl2 was rinsed with a NaHSO3 solution
  3. customdried
  4. concentrationconcentrated
  5. additioncyclohexane was added

Sources & evidence

ORD record
ord-345c017f3a8b405a8e8100fe5c8afcba
Source dataset
uspto-grants-2012_02
Patent number
US08124793B2

Reaction notes

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