Toluene → (2,2,2-Trifluoro-1-methylethyl) 2-naphthalenesulfonate

HRID 1461411Notes

Reaction equation

HRID 1461411 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].CC1C=CC=CC=1.[F:22][C:23]([F:28])([F:27])[CH:24]([OH:26])[CH3:25].[H-].[Na+]>O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([O:26][CH:24]([CH3:25])[C:23]([F:28])([F:27])[F:22])(=[O:12])=[O:13]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 71252-Naphthalenesulfonyl chlorideHCID 97741,1,1-Trifluoro-2-propanolHCID 24758Sodium hydride

Product 1

HCID 53934608(2,2,2-Trifluoro-1-methylethyl) 2-naphthalenesulfonateYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (ice-bath) suspension of 41.7 parts of 2-naphthalenesulfonyl chloride in 174 parts of methylbenzene were added dropwise 20.0 parts of 1,1,1-trifluoro-2-propanol. After stirring for 1 hour, there was added dropwise a mixture of 9.6 parts of a dispersion of sodium hydride in mineral oil (50%) and some methylbenzene while cooling on ice. Subsequently, the whole was diluted dropwise with water. The organic layer was separated, dried, filtered and evaporated, yielding 53.2 parts (99.9%) of (2,2,2-trifluoro-1-methylethyl) 2-naphthalenesulfonate (interm. 28).

Workup

  1. temperatureTo a cooled
  2. additionthere was added dropwise
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5906a57a90264de999326fae798dbf6d
Source dataset
uspto-grants-1991_12
Patent number
US05075309

Reaction notes

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