1,2-Diisopropyloxy benzene synthesis

Yield:1698-98-2 94%

Reaction Conditions:

with potassium carbonate in acetone; for 48 h;Reflux;Williamson synthesis;

Steps:

4.2.2. 1,2-Diisopropoxybenzene (1b)

A mixture of catechol (11.0 g, 100 mmol), 2-iodopropane (30.0 mL, 300 mmol), and K₂CO₃ (48.5 g, 351 mmol) in acetone (100 mL) was refluxed for 2 days and the reaction progress monitored by TLC. The salts were filtered off rinsing with acetone and the filtrate concentrated. The residue was partitioned between H₂O (100 mL) and Et₂O (80 mL), and the product extracted with Et₂O (2×80 mL). The organic layer was washed with 1 M NaOH (50 mL), dried (Na₂SO₄), and concentrated. Kugelrohr distillation (120 °C, 10 mbar) afforded a colorless liquid (18.3 g, 94%); R_f (toluene) 0.6; δ_H 1.33 (12H, d, J 6.1 Hz, 4Me), 4.46 (2H, sept, J 6.1 Hz, 2CH), 6.87-6.96 (4H, m); δ_C 22.2, 72.1, 118.4, 121.7, 149.2. ¹H NMR is in accordance with the literature data.¹⁸

References:

Stephan, Michel;Zupancic, Borut;Mohar, Barbara [Tetrahedron,2011,vol. 67,# 34,p. 6308 - 6315] Location in patent:experimental part