Methanol → p-Ethynyltoluene

HRID 1837398Notes

Reaction equation

HRID 1837398 reaction equation
C[Si](C)(C)[C:3]1[CH:8]=[CH:7][C:6](C)=[C:5]([C:10]#[CH:11])[CH:4]=1.[OH-].[K+].[CH3:16]O>O>[C:8]1([CH3:16])[CH:3]=[CH:4][C:5]([C:10]#[CH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 86591176HCID 86591176, compound

Product 1

HCID 13018p-EthynyltolueneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

34.7 g (0.184 mol) of 4-trimethylsilyl ethynyl toluene was dissolved in 500 ml of methanol in a 1 L round-bottomed flask equipped with a stirrer. 10 ml of 20% KOH in water was added to the resulting solution. The reaction mixture was then stirred at room temperature for 5 hours. After the reaction was completed, water were poured into the flask. The reaction mixture was then extracted with ethyl ether several times. The combined extract was washed with water several times, and then dried with anhydrous magnesium sulfate. The solvent was removed, to give 21 g (98% yield) of yellow liquid.

Workup

  1. customequipped with a stirrer
  2. extractionThe reaction mixture was then extracted with ethyl ether several times
  3. extractionThe combined extract
  4. washwas washed with water several times
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-37e4aac390114fd596c7e57ded24ef4d
Source dataset
uspto-grants-2004_08
Patent number
US06780950B2

Reaction notes

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