Réaction #546284

Équation de réaction

4-phenylphenol

potassium tert-butoxide

Sodium iodide

toluene-4-sulfonic acid but-3-ynyl ester

→

oil

Rendement 14.0%

4-But-3-ynyloxy-biphenyl

Rendement 14.0%

Solvants

toluene

diethyl ether

Conditions de réaction

Traitement

1. 1
   Températurethe mixture heated
2. 2
   Températureto reflux for 24 hours
3. 3
   Lavagewashed with water (2×20 mL)
4. 4
   SéchageThe organic layer was dried (MgSO4)
5. 5
   Concentrationconcentrated under vacuum
6. 6
   AutreThe residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 3:1, Rf0.57)

Mode opératoire

A solution of 4-phenylphenol (0.774 g, 4.55 mmol) and potassium tert-butoxide (0.51 g, 4.55 mmol) in toluene (20 mL) was stirred for 1 h at room temperature. Sodium iodide (0.068 g, 0.45 mmol) and toluene-4-sulfonic acid but-3-ynyl ester (1.02 g, 4.55 mmol) were added, and the mixture heated to reflux for 24 hours. The mixture was cooled to room temperature, diluted with diethyl ether (20 mL), washed with water (2×20 mL). The organic layer was dried (MgSO4) and concentrated under vacuum. The residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 3:1, Rf0.57) to give an oil (140 mg, 14%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.50 (m, 4H), 7.46–7.38 (m, 2H), 7.32 (d, 1H, J=7.3), 7.02–6.95 (m, 2H), 4.15 (t, 2H, J=7.0), 2.71 (dt, 2H, J=2.7, 7.3), 2.06 (t, 1H, J=2.7).

Source