Toluene → HCID 22352715, compound

HRID 992167

Reaction equation

HRID 992167 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[CH2:10]([C:13]([F:37])([F:36])[C:14]([F:35])([F:34])[C:15]([F:33])([F:32])[C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[CH2:11][OH:12].C1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[K+]>[C:1]([O:5][C:6](=[O:9])[CH2:7][O:12][CH2:11][CH2:10][C:13]([F:36])([F:37])[C:14]([F:34])([F:35])[C:15]([F:32])([F:33])[C:16]([F:30])([F:31])[C:17]([F:28])([F:29])[C:18]([F:26])([F:27])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1140Toluene2×HCID 696191,1,2,2-Tetrahydroperfluoro-1-decanolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 22352715HCID 22352715, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

10.51 g (53.9 mmol) of bromoacetic acid-tert-butyl ester is added in drops to a mixture of 10 g (21.55 mmol) of 1H,1H,2H,2H-perfluorodecan-1-ol and 0.73 g (2.15 mmol) of tetrabutylammonium hydrogen sulfate in 100 ml of 60% potassium hydroxide solution/50 ml of toluene while being stirred vigorously at 0° C. It is stirred for 1 hour at 0° C. 200 ml of toluene is added, the aqueous phase is separated and extracted twice with 50 ml of toluene each. The combined organic phases are dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel (mobile solvent: hexane/dichlormethane/acetone=20/10/1).

Workup

  1. stirringIt is stirred for 1 hour at 0° C
  2. customthe aqueous phase is separated
  3. extractionextracted twice with 50 ml of toluene each
  4. customThe combined organic phases are dried on magnesium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue is chromatographed on silica gel (mobile solvent: hexane/dichlormethane/acetone=20/10/1)

Sources & evidence

ORD record
ord-358a9c4b9de84f8795132100f5476ebc
Source dataset
uspto-grants-2002_10
Patent number
US06468502B1

Linked notes

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