Hydrochloric Acid → HCID 86642237, compound

HRID 1943569Notes

Reaction equation

HRID 1943569 reaction equation
C([O:6][CH2:7][CH2:8][CH2:9][S:10]([O-:13])(=[O:12])=[O:11])(=O)C(C)=C.[C:14]1([S+:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[O-].[Na+].Cl.C(C(C)=O)C(C)C>CO>[OH:6][CH2:7][CH2:8][CH2:9][S:10]([O-:13])(=[O:12])=[O:11].[C:27]1([S+:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7909Methyl Isobutyl KetoneHCID 10942334Sodium MethoxideHCID 86642236HCID 86642236, compound

Product 1

HCID 86642237HCID 86642237, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 100 g of methylene chloride were added 2.5 g (10 mmol) of a potassium salt of 3-sulfopropyl methacrylate and 23 g (10 mmol) of an aqueous solution of triphenylsulfonium chloride prepared in Synthesis Example 1-1. The mixture was stirred at room temperature for 30 minutes. The organic layer was taken out and washed with water. It was combined with ethanol and concentrated in vacuum while azeotroping off the residual water. There was obtained 3.3 g of triphenylsulfonium 3-methacryloyloxypropanesulfonate. To 3.3 g of triphenylsulfonium 3-methacryloyloxypropanesulfonate were added 100 mg (0.6 mmol) of 28 wt % sodium methoxide in methanol and 15 g of methanol. The mixture was stirred at room temperature for 3 days. Then 70 mg of 35% aqueous hydrochloric acid was added to quench the reaction. The reaction solution was combined with methyl isobutyl ketone and concentrated in vacuum while distilling off the residual water. Diisopropyl ether was added to the residue for recrystallization. The crystals were collected and dried, obtaining the target compound, triphenylsulfonium 3-hydroxypropanesulfonate. White crystals, 2.1 g, yield 52%. The compound, designated PAG intermediate 2, has the following structure.

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationconcentrated in vacuum
  4. distillationwhile distilling off the residual water
  5. additionDiisopropyl ether was added to the residue for recrystallization
  6. customThe crystals were collected
  7. customdried

Sources & evidence

ORD record
ord-4a1dc4b0649d4c60a0a1bf3408efe831
Source dataset
uspto-grants-2013_03
Patent number
US08394570B2

Reaction notes

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