Water → Tetra(Cyanoethoxymethyl) Methane

Participants

Reaction Conditions

Reaction Steps

Pentaerythritol (6.84 g, 50 mmol) was dissolved in 20 ml dioxane and 2 ml water and mixed up with 40% aqueous potassium hydroxide solution (w/v, 1 ml). After cooling to 0° C. in an ice bath, acrylonitrile (16.2 g, 300 mmol) was added and the mixture stirred for 48 h at room temperature. Solvents were evaporated, the remaining oil was diluted in 100 ml dichloromethane and washed with 10% aqueous sodium chloride solution (w/v, 50 ml). After re-extraction of the aqueous layer with dichloromethane (2×25 ml), the combined organic layers were dried over sodium sulfate and intensively evaporated. The nitrile was obtained as a colorless syrup: yield: 14.32 g (41 mmol, 82%). 1H-NMR (400 MHz, CDCl3) δ 2.60 (t, 8 H,—CH2CN), 3.50 (s, 8 H, —CqCH2O—), 3.65 (t, 8 H, —OCH2—). 13C-NMR (100 MHz, CDCl3) δ 18.86 (—CH2CN), 45.68 (Cq), 65.88 (—OCH2—), 68.82 (CqCH2O—), 118.22 (CN).

Provenance & Evidence