Hydrochloric Acid → HCID 22465771, compound

HRID 1936337Notes

Reaction equation

HRID 1936337 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.FC(F)(F)S(O[CH2:23][CH2:24][C:25]([F:37])([F:36])[C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])(=O)=O.Cl>C1C=CC=CC=1.C(COC)OC>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:23][CH2:24][C:25]([F:36])([F:37])[C:26]([F:34])([F:35])[C:27]([F:32])([F:33])[C:28]([F:31])([F:30])[F:29])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 71124,4'-DihydroxybiphenylHCID 24758Sodium hydrideHCID 224657573,3,4,4,5,5,6,6,6-Nonafluorohexyl trifluoromethanesulfonate

Product 1

HCID 22465771HCID 22465771, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

First, 3.0 g of 60% sodium hydride and 120 ml of dehydrated dimethoxyethane were put in an argon-replaced 300 ml flask. Then, 9.93 g of 4,4′-dihydroxybiphenyl was added while icing, and stirred at room temperature for two hours. The reaction solution was cooled again to −60° C., and 28.7 g of 2-(perfluorobutyl)ethyl trifluoromethanesulfonate was dropped into the reaction solution. After the resultant reaction solution was left to resume room temperature, it was stirred for 12 hours. After the reaction, dilute hydrochloric acid and benzene were added to the reaction solution to separate an organic layer. The organic layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography (eluent:benzene/ethyl acetate=9/1), and recrystallized from toluene to obtain 6.26 g (Y: 27.1%) of 4-hydroxy-4′-[2-(perfluorobutyl)ethyloxy]biphenyl. The purity of the resultant compound was 98.4% as measured by GC.

Workup

  1. temperatureThe reaction solution was cooled again to −60° C.
  2. customAfter the resultant reaction solution
  3. waitwas left
  4. customto resume room temperature
  5. stirringit was stirred for 12 hours
  6. additionwere added to the reaction solution
  7. customto separate an organic layer
  8. washThe organic layer was washed with a saturated brine
  9. dry with materialdried with sodium sulfate
  10. distillationThe solvent was then distilled off
  11. customThe residue was purified by silica gel column chromatography (eluent:benzene/ethyl acetate=9/1)
  12. customrecrystallized from toluene

Sources & evidence

ORD record
ord-cd04289144b74407a9a4b1c61334cdc3
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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