Benzene → 1-Ethynyl-4-methoxynaphthalene

HRID 1287929Notes

Reaction equation

HRID 1287929 reaction equation
C1([Li])C=CC=CC=1.Br[CH:9]=[CH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1.C1C=CC=CC=1>O>[C:10]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1)#[CH:9]

Participants

5

Reactant 3

HCID 241BenzeneHCID 544133521-(2-Bromoethenyl)-4-methoxynaphthaleneHCID 178506676HCID 178506676, compound

Product 1

HCID 123269971-Ethynyl-4-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenyllithium (164 ml. of 2.1 M, 0.345 mol.) was added dropwise to a solution of 35.9 g. (0.138 mol.) of 1-(2-bromoethenyl)-4methoxynaphthalene in 120 ml. of refluxing dry benzene under a nitrogen atmosphere. After addition the reaction mixture was refluxed for 30 minutes, then ice and water were slowly added. The mixture was shaken, the layers separated and the organic phase was washed with water and saturated sodium chloride solution, dried (MgSO4) and evaporated to give 1-ethynyl-4-methoxynaphthalene.

Workup

  1. additionAfter addition the reaction mixture
  2. temperaturewas refluxed for 30 minutes
  3. customthe layers separated
  4. washthe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-b5415cf9ad40412ea1b94a460feec1d8
Source dataset
uspto-grants-1976_10
Patent number
US03985896

Reaction notes

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