1-Naphthol → Naphthalene, 1-(2-propynyloxy)-

HRID 1742723Notes

Reaction equation

HRID 1742723 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:14](Br)[C:15]#[CH:16]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CCOCC>[CH2:16]([O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:15]#[CH:14]

Participants

7

Reactant 3

HCID 70051-NaphtholHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 29132Naphthalene, 1-(2-propynyloxy)-Yield 63.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Into a reaction flask fitted with a stirrer, a thermometer, a nitrogen gas inlet tube and a reflux condenser, was placed 21.259 parts of 1-naphthol, 53.086 parts of deionized water, 6.675 parts of NaOH and 0.120 part of tetrabutylammoniumbromide and to this mixture, 18.859 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 a mixture of ether and deionized water and the ether layer was separated, added with magnesium sulfate and kept stand overnight. After filtering off magnesium sulfate, the ether solvent was removed by an evaporator and the residue was subjected to a column chromatography (silica gel 200 mesh) to obtain a purified 1propargyloxynaphthalene. Yield 63.6%

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. customthe ether layer was separated
  5. additionadded with magnesium sulfate
  6. filtrationAfter filtering off magnesium sulfate
  7. customthe ether solvent was removed by an evaporator

Sources & evidence

ORD record
ord-c9edb583e7814281bf10d4d4c0b0d3eb
Source dataset
uspto-grants-1994_08
Patent number
US05340931

Reaction notes

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