2-[4-(dimethylamino)phenyl]ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This monomer was synthesized in a manner analogous to the published method used for the synthesis of 4-(dimethylamino)benzyl methacrylate. Thus, 4.55 g (0.0435 mol) methacryloyl chloride in 4.55 g benzene was added dropwise to a solution of 5.0 g (0.03 mol) 4-dimethylaminophenethyl alcohol, 3.64 g (0.036 mol) triethylamine, and 8.7 g benzene in the presence of p-benzoquinone and CuCl(I) with stirring and cooling, keeping the temperature below 15° C. The reaction mixture was left to stir for one hour in a room temperature water bath (about 25° C.). The solution was filtered to remove triethylamine hydrochloride. The benzene filtrate was washed with water and then with saturated sodium carbonate solution, dried over sodium sulfate anhydrous, filtered, and the benzene removed with the rotary evaporator (water bath 20-25° C.). The monomer was distilled in vacuo in the presence of CuCl(I) and 2,2-diphenyl-1-picrylhydrazyl (DPPH), bp=115-122° C./95-100, μHg. The monomer was recrystallized from petroleum ether, mp=42-43° C. The analysis for nitrogen showed 5.86% N (calc. 6.00). NMR δ(ppm): 1.9 (s, 3, CH2═C(CH3)—); 2.8 (m, 2, —CH2—CH2—C6H4—); 2.9 (s, 6, CH3)2); 4.2-4.3 (m, 2, —(O)C—O—CCH2—CH2—); 5.5, 6.1 (d, s, 2, CH2═C); 6.7, 7.1 (d, d, 4, aromitic H). This monomer was synthesized in a manner analogous to the published method cooling the temperature below 15° C The reaction mixture was left to stir for one hour in a room temperature water bath (about 25° C.) The solution was filtered to remove triethylamine hydrochloride The benzene filtrate was washed with water with saturated sodium carbonate solution, dried over sodium sulfate anhydrous filtered the benzene removed with the rotary evaporator (water bath 20-25° C.) The monomer was distilled in vacuo in the presence of CuCl(I) and 2,2-diphenyl-1-picrylhydrazyl (DPPH), bp=115-122° C./95-100, μHg The monomer was recrystallized from petroleum ether, mp=42-43° C

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: K-t-BuO (2.27 g, 20.3 mmol) was added to a stirred solution of 4-(dimethylamino)phenethyl alcohol (3.55 g, 21.5 mmol) in dioxane (35 mL) at 0° C. (ice-bath). After being stirred for 5 min at 0° C. and 12 min at room temperature, the mixture was chilled to 0° C. (ice-bath) and 2,6-dichloropyrazine (2.62 g, 17.6 mmol) was added. The reaction mixture was stirred at 0° C. for 5 min and at room temperature for 20 min and diluted with dichloromethane/ether (1:1). Filtration through a pad of Celite, covered with K2CO3, and concentration in vacuo furnished a yellow oil. This material was purified by chromatography on silica gel (15×5 cm) using n-hexane/ethyl acetate (85:15). A second chromatograhic run on silica gel (14×5 cm) using n-hexane/ethyl acetate (88:12) furnished 3.91 g (80%) of the title compound as a colorless oil. Anal. (C14H16ClN3O) C, H, N. was added The reaction mixture was stirred at 0° C. for 5 min and at room temperature for 20 min Filtration through a pad of Celite covered with K2CO3, and concentration in vacuo furnished a yellow oil This material was purified by chromatography on silica gel (15×5 cm)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: K-t-BuO (2.27 g, 20.3 mmol) was added to a stirred solution of 4-(dimethylamino)phenethyl alcohol (3.55 g, 21.5 mmol) in dioxane (35 mL) at 0° C. (ice-bath). After being stirred for 5 min at 0° C. and 12 min at room temperature, the mixture was chilled to 0° C. (ice-bath) and 2,6-dichloropyrazine (2.62 g, 17.6 mmol) was added. was added