Potassium Hydroxide → 4-tert-Butylphenylacetylene

HRID 439925Notes

Reaction equation

HRID 439925 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)(C)C.[OH-].[K+]>C(O)(C)C>[C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:6]#[CH:5])=[CH:12][CH:11]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14989664((4-(tert-Butyl)phenyl)ethynyl)trimethylsilane2×

Product 1

HCID 27573024-tert-Butylphenylacetylene

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 1.44 g (6.23 mmol) of trimethylsilyl(4-tert-butyl)phenylethyne (Compound 21) in 5 ml of isopropanol was added 10 ml of 1N aqueous KOH and the mixture then stirred at room temperature for 6.5 hours. The isopropanol was removed under vacuum and the residue extracted with ether. The ether extract was washed with dilute HCl until the washings were acidic. The ether solution was then successively washed with water, saturated NaCl and NaHCO3 solutions and then dried (MgSO4). Solvent was then removed in-vacuo to give the title compound as a colorless oil. PMR (CDCl3): & 1.34 (9H, s), 3.05 (1H, s), 7.37 (2H, d, J-8.2 Hz), 7.46 (2H, d, J-8.2 Hz).

Workup

  1. customThe isopropanol was removed under vacuum
  2. extractionthe residue extracted with ether
  3. extractionThe ether extract
  4. washwas washed with dilute HCl until the washings
  5. washThe ether solution was then successively washed with water, saturated NaCl and NaHCO3 solutions
  6. dry with materialdried (MgSO4)
  7. customSolvent was then removed in-vacuo

Sources & evidence

ORD record
ord-f6627850d2fd4a99a5e375ca78bbc53a
Source dataset
uspto-grants-1996_05
Patent number
US05516904

Reaction notes

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