Pyrogallol → 1,3,5-Tris(2-propynyloxy)benzene

Participants

Reaction Steps

Trihydroxybenzene (0.5 g 3.08 mmol) and propargyl bromide (4 ml, 12 mmol) were dissolved in 10 mL THF, dry potassium carbonate (3.75 g, 12 mmol) and catalytic amount 18-crown-6-ether was added. The reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated and the mixture was dissolved in DCM, washed with brine. Concentration afforded crude product which was further purified by silica gel chromatography (1:2 ethyl acetate:hexane), giving compounds 17 0.54 g (72%). TLC (1:2 ethyl acetate:hexane): Rf=0.36. 1H NMR (400 MHz, CDCl3) δ 6.26 (3H, s), 4.64 (6H, d, J=2.4 Hz), 2.54 (3H, t, J=2.4 Hz). 13C NMR (100 MHz, CDCl3) δ 159.41, 95.50, 78.35, 75.88, 56.04. Low-resolution mass spectrum (ESI) calcd. for C15H13O3 [M+H]+: 241.08. Found: 241.00.

Provenance & Evidence