Guaiacol → 1-(2-Chloroethoxy)-2-methoxybenzene

Participants

Reaction Conditions

Reaction Steps

Guaiacol (6.2 g, 50 mmol) and 1-bromo-2-chloro-ethane (8.4 mL, 100 mmol) were mixed thoroughly and heated at 100° C. for 30 minutes. Then, 31 ml of 1.6 N NaOH aqueous solution was added into the mixture to bring the pH to about 7.0. After cooling, the mixture was extracted with chloroform. The chloroform layer was partitioned with 20% NaOH aqueous solution, water and saturated NaCl aqueous solution in sequence. The organic portion was dried with anhydrous sodium sulfite and evaporated to dryness to obtain O-(2-chloroethyl)guaiacol (18) (9 g; yield 96%). Rf 0.67 (chloroform with saturated ammonia water); IR (KBr) νmax 2934 (m), 1593 (s), 1504 (s), 1455 (s), 1254 (s), 1224 (s), 1178 (s), 1125 (s), 1028 (m) cm−1; 1H NMR (CDCl3, 400MHz): δ 6.94 (4H, m), 4.26 (2H, t, J=6.3Hz), 3.85 (3H, s, 2-OMe), 3.81 (2H, t, J=6.3Hz).

Provenance & Evidence