Potassium Hydroxide → 1-Ethynyl-4-propylbenzene

HRID 493031

Reaction equation

HRID 493031 reaction equation
[OH-].[K+].[CH2:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][Si](C)(C)C)=[CH:8][CH:7]=1)[CH2:4][CH3:5]>CO>[CH2:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[CH:13])=[CH:10][CH:11]=1)[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 193534011-(4-n-Propylphenyl)-2-trimethylsilylacetylene

Product 1

HCID 27751331-Ethynyl-4-propylbenzeneYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methanol (150 ml) and an aqueous solution of 1N-potassium hydroxide (100 ml) were added to 14.2 g (65.7 mmol) of 1-(4-n-propylphenyl)-2-trimethylsilylacetylene synthesized in the step (i), and the mixture was subjected to hydrolysis with vigorously stirring overnight. After completion of the reaction, methanol was removed and the resultant residue was extracted with hexane. After removing hexane from the hexane phase, the resultant residue was washed with water to give 9.4 g (65.3 mmol) of 4-n-propylphenylacetylene.

Workup

  1. customsynthesized in the step (i)
  2. customthe mixture was subjected to hydrolysis
  3. customwas removed
  4. extractionthe resultant residue was extracted with hexane
  5. customAfter removing hexane from the hexane phase
  6. washthe resultant residue was washed with water

Sources & evidence

ORD record
ord-b6c976575fa84c26b28100f46a3d5f38
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Linked notes

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