Hydrochloric Acid → HCID 22465771, compound

HRID 2395200Notes

Reaction equation

HRID 2395200 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>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

6

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 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In a Schlenk tube whose content had been replaced with Ar, 9.0 g of 60% sodium hydride and 400 ml of dry dimethoxyethane were placed. While this solution was being cooled with ice water, 29.8 g of 4,4'-dihydroxybiphenyl was added. Thereafter, the reaction solution was allowed to warm up to room temperature, and was stirred for two hours. Thereafter, the reaction solution was cooled to -60° C. After 86 g of 2-(perfluorobutyl)ethyl trifluoromethane sulfonate was added dropwise to the reaction solution, the reaction solution was allowed to warm up to room temperature, and was stirred overnight. Subsequently, the reaction solution was poured into dilute hydrochloric acid, and an organic layer was extracted with benzene. After the benzene layer was washed with water and dried over sodium sulfate anhydrous, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: benzene), and recrystallized from toluene to give 18.8 g of 4-hydroxy-4'-[2-(perfluorobutyl)ethyloxy]biphenyl (Y: 27.1%). The purity of the compound thus obtained was 98.4% by GC.

Workup

  1. additionwas added
  2. temperatureThereafter, the reaction solution was cooled to -60° C
  3. temperatureto warm up to room temperature
  4. stirringwas stirred overnight
  5. extractionan organic layer was extracted with benzene
  6. washAfter the benzene layer was washed with water
  7. dry with materialdried over sodium sulfate anhydrous
  8. distillationthe solvent was distilled away
  9. customThe residue was purified by silica gel column chromatography (eluent: benzene)
  10. customrecrystallized from toluene

Sources & evidence

ORD record
ord-8b3315d4a87446fd969bc44c18c1a6f5
Source dataset
uspto-grants-1998_09
Patent number
US05814378

Reaction notes

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