Hydrochloric Acid → Triphenylsulfonium 2-hydroxyethanesulfonate

HRID 1943567Notes

Reaction equation

HRID 1943567 reaction equation
C([O:9][CH2:10][CH2:11][S:12]([O-:15])(=[O:14])=[O:13])(=O)C1C=CC=CC=1.[C:16]1([S+:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O-].[Na+].Cl.C(C(C)=O)C(C)C>CO>[OH:9][CH2:10][CH2:11][S:12]([O-:15])(=[O:14])=[O:13].[C:29]1([S+:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7909Methyl Isobutyl KetoneHCID 10942334Sodium MethoxideHCID 86642233Triphenylsulfonium 2-benzoyloxyethanesulfonate

Product 1

HCID 86642235Triphenylsulfonium 2-hydroxyethanesulfonateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 2.9 g (6 mmol) of triphenylsulfonium 2-benzoyloxyethanesulfonate prepared in Synthesis Example 1-11, 56 mg (0.3 mmol) of 28 wt % sodium methoxide in methanol, and 15 g of methanol was stirred at room temperature for 12 hours. To the reaction solution, 30 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 2-hydroxyethanesulfonate. White crystals, 2.1 g, yield 96%. The compound, designated PAG intermediate 1, 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-b66e3d5ba7ff47b59d4b545424abbfdd
Source dataset
uspto-grants-2013_03
Patent number
US08394570B2

Reaction notes

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