Potassium Hydroxide → 4-tert-Butylphenylacetylene

HRID 2226717Notes

Reaction equation

HRID 2226717 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 23) 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): δ1.34 (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-95989be25cf84df5a7b36d9ba25edf8d
Source dataset
uspto-grants-1994_09
Patent number
US05349105

Reaction notes

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