(+-)-Mercaptosuccinic acid → 2-Mercaptosuccinic acid bis-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) ester

HRID 641094Notes

Reaction equation

HRID 641094 reaction equation
[SH:1][CH:2]([CH2:6][C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].[CH2:10]([C:13]([F:31])([F:30])[C:14]([F:29])([F:28])[C:15]([F:27])([F:26])[C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[CH2:11]O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:30][C:13]([F:31])([C:14]([F:29])([F:28])[C:15]([F:27])([F:26])[C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[CH2:10][CH2:11][O:4][C:3](=[O:5])[CH:2]([SH:1])[CH2:6][C:7]([O:9][CH2:11][CH2:10][C:13]([F:30])([F:31])[C:14]([F:28])([F:29])[C:15]([F:26])([F:27])[C:16]([F:24])([F:25])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])=[O:8]

Participants

5

Reactant 2

HCID 6268(+-)-Mercaptosuccinic acidHCID 695373,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol

Product 1

HCID 875035232-Mercaptosuccinic acid bis-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) esterYield 100%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Mercaptosuccinic acid (Aldrich) (12.5 g, 0.083 mole) and 1H,1H,2H,2H-perfluorooctan-1-ol (Fluorochem Ltd.) (60.6 g, 0.166 mole) were suspended in toluene (400 ml). p-Toluene sulfonic acid hydrate (Aldrich) (0.36 g) was added and the mixture refluxed under argon atmosphere for 72 hours in a flask equipped with a Dean & Stark reflux condenser. The solution was allowed to cool and the toluene was removed by evaporation under reduced pressure. The resulting oil was redissolved in ethyl acetate (1000 ml) and washed with saturated aqueous sodium hydrogen carbonate (800 ml). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and evaporated to give 2-mercaptosuccinic acid bis-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) ester as a pale yellow oil (66.2 g, 100% yield).

Workup

  1. temperaturethe mixture refluxed under argon atmosphere for 72 hours in a flask
  2. customequipped with a Dean & Stark
  3. temperaturereflux condenser
  4. temperatureto cool
  5. customthe toluene was removed by evaporation under reduced pressure
  6. dissolutionThe resulting oil was redissolved in ethyl acetate (1000 ml)
  7. washwashed with saturated aqueous sodium hydrogen carbonate (800 ml)
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-b8918341361a48a6aaa1ef6b41966476
Source dataset
uspto-grants-2010_04
Patent number
US07695783B2

Reaction notes

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