4-Hydroxybiphenyl → HCID 19007818, compound

HRID 1742727Notes

Reaction equation

HRID 1742727 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:16](Br)[C:17]#[CH:18].S([O-])([O-])(=O)=[O:21].[Mg+2]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[CH2:16]([O:21][C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][CH:2]=[CH:3][CH2:4]1)[C:17]#[CH:18]

Participants

8

Reactant 4

HCID 71034-HydroxybiphenylHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide2×HCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 19007818HCID 19007818, compoundYield 53.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a reaction flask fitted with a stirrer, a thermometer, a nitrogen gas inlet tube and a reflux condenser, were placed 24.140 parts of p-hydroxybiphenyl, 51.120 parts of deionized water, 6.427 parts of NaOH and 0.127 part of tetrabutylammonium bromide and to this mixture, 18.161 parts of propargyl bromide was added dropwise and reacted at 80° C. for 6 hours. After completion of the reaction, the content was treated with an aqueous NaOH solution and then subjected to a fractionation with ethyl acetate. Thereafter, magnesium sulfate was added and the mixture was kept standing overnight to effect dehydration. After filtering off magnesium sulfate, the solvent was removed off by an evaporator and the residue was subjected to a column chromatography (silica gel 200 mesh) to obtain a purified 1-propargyloxybiphenyl. Yield 53.1%

Workup

  1. customInto a reaction flask fitted with a stirrer
  2. customreacted at 80° C. for 6 hours
  3. customAfter completion of the reaction
  4. filtrationAfter filtering off magnesium sulfate
  5. customthe solvent was removed off by an evaporator

Sources & evidence

ORD record
ord-cd798c18164a4ca491e229aa683269ae
Source dataset
uspto-grants-1994_08
Patent number
US05340931

Reaction notes

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