2,2-Bis(trifluoromethyl)oxirane → Sodium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

HRID 2360751Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1([C:6]([F:9])([F:8])[F:7])[CH2:5][O:4]1.[S:12]([O-:15])([OH:14])=[O:13].[Na+:16]>O>[F:1][C:2]([F:11])([F:10])[C:3]([OH:4])([C:6]([F:9])([F:8])[F:7])[CH2:5][S:12]([O-:15])(=[O:14])=[O:13].[Na+:16]

Participants

Conditions

Temperature: 40 °C

Procedure

Using the 2,2-bis(trifluoromethyl)oxirane prepared in Synthesis Example 1-2, synthesis was carried out in accordance with the procedure described in US 20100209827. A mixture of 30 g of 2,2-bis(trifluoromethyl)oxirane, 26 g of sodium hydrogensulfite, and 120 g of water was stirred at 40° C. for 10 hours, obtaining an aqueous solution of sodium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate. Subsequently, 34 g of an aqueous solution of 2,000 g/mol of triphenylsulfonium chloride and 400 g of methylene chloride were added to the aqueous solution, which was stirred for 4 hours at room temperature. At the end of stirring, the organic layer was taken out, washed with water, and concentrated under reduced pressure. The concentrate was combined with methyl isobutyl ketone and concentrated again under reduced pressure to distill off the residual water. To the residue, diisopropyl ether was added for recrystallization, obtaining 74 g of triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate (yield 85%).

Workup

customprepared in Synthesis Example 1-2, synthesis

Sources & evidence

ORD record: ord-5cd9c5403e2f48daa82ebe75a31da2fa
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686166B2

Reaction notes

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