Toluene → 1-Ethynylpyrene

HRID 1095218Notes

Reaction equation

HRID 1095218 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]2[C:16]3=[C:17]4[C:7]([CH:8]=[CH:9][CH:10]=[C:11]4[CH:12]=[CH:13]2)=[C:6](C#CCO)[CH:5]=[C:4]3C=1C.[OH-].[Na+].[C:25]1(C)C=CC=C[CH:26]=1>>[C:6]1([C:25]#[CH:26])[C:5]2[C:12]3=[C:13]4[C:14](=[CH:16][CH:4]=2)[CH:15]=[CH:2][CH:1]=[C:8]4[CH:9]=[CH:10][C:11]3=[CH:17][CH:7]=1

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 14798Sodium HydroxideHCID 86761528HCID 86761528, compound

Product 1

HCID 1549051-EthynylpyreneYield 58%

Conditions

Temperature
120 °C

Procedure

1.5 g (5.28 mmol) of Dimethylhydroxymethyl-9-pyrenylacetylene and 222 mg (5.54 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 50 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 26 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 0.67 hour. Toluene was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure by an evaporator. The crude reaction product was purified by column chromatography (Hexane/AcOEt=10/1) using silica gel to give 1-pyrenylethyne as an orange-color solid (0.69 g, yield: 58%).

Workup

  1. customequipped with a reflux condenser
  2. washthe mixture was washed with a saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure by an evaporator
  5. customThe crude reaction product
  6. customwas purified by column chromatography (Hexane/AcOEt=10/1)

Sources & evidence

ORD record
ord-40aedb6d3a314b46bac8270ebcae5246
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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