Sodium Hydroxide → HCID 23708595, compound

HRID 1379298Notes

Reaction equation

HRID 1379298 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[S:10]([O:13]C(C)C)(=[O:12])=[O:11].[OH-].[Na+:20]>O1CCCC1.O>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[S:10]([O-:13])(=[O:11])=[O:12].[Na+:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11832867Isopropyl 2-trifluoromethyl-6-methylbenzenesulfonate2×

Product 1

HCID 23708595HCID 23708595, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 83 g of the crude isopropyl 2-trifluoromethyl-6-methylbenzenesulfonate (which contained about 10% of isopropyl 2-trifluoromethylbenzenesulfonate) in 300 mL of tetrahydrofuran was treated with a solution of 24.8 g of 50% aqueous sodium hydroxide in 150 mL of water and heated to reflux for 4 hours, then stirred at room temperature overnight. The mixture was assayed by capillary GC (10 m DB-1, 100°-250° C. at 20° C./min) to ascertain that the isopropyl 2-trifluoromethyl-6-methylbenzenesulfonate was consumed. The tetrahydrofuran was removed in vacuo, then the remainder was poured into 100 mL of water and 200 mL of hexane. The aqueous phase was washed with hexane, then the water removed in vacuo to yield 71 g sodium 2-trifluoromethyl-6-methylbenzenesulfonate as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customwas assayed by capillary GC (10 m DB-1, 100°-250° C. at 20° C./min)
  4. customwas consumed
  5. customThe tetrahydrofuran was removed in vacuo
  6. additionthe remainder was poured into 100 mL of water and 200 mL of hexane
  7. washThe aqueous phase was washed with hexane
  8. customthe water removed in vacuo

Sources & evidence

ORD record
ord-962d6d7eb17c4ecdaae6666ad10fedf5
Source dataset
uspto-grants-1997_09
Patent number
US05670691

Reaction notes

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