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Toluene → HCID 15406176, compound

HRID 1764986
Notes
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Reaction equation

HRID 1764986 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[CH2:10]([C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[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:24])([F:25])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:17])([F:19])[F:18])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1140Toluene2×HCID 748831-Hexanol, 3,3,4,4,5,5,6,6,6-nonafluoro-HCID 79177tert-Butyl bromoacetate

Product 1

HCID 15406176HCID 15406176, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst
HCID 14797
Potassium Hydroxide
Solvent

Conditions

Temperature
0 °C

Procedure

29.54 g (151.5 mmol) of bromoacetic acid-tert-butyl ester is added in drops to a mixture of 20 g (75.73 mmol) of 1H,1H,2H,2H-perfluorohexan-1-ol and 2.57 g (7.57 mmol) of tetrabutylammonium hydrogen sulfate in 300 ml of 60% aqueous potassium hydroxide solution/200 ml of toluene while being stirred vigorously at 0° C. It is stirred for 1 hour at 0° C. 100 ml of toluene is added, the aqueous phase is separated and extracted twice with 50 ml of toluene. 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/dichloromethane/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
  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/dichloromethane/acetone=20/10/1)

Sources & evidence

ORD record
ord-215f1c6da231493f906efc545ade8d6f
Source dataset
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07226578B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes