4-Hydroxybenzaldehyde → p-(Octyloxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

4-hydroxybenzaldehyde (8.2 mmols), 1-bromooctane (12.3 mmols) and cesium carbonate (16.4 mmols) were dissolved in DMF (13.7 mmols). The mixture was then heated to 80° C. and stirred for 3 hours. After this time, the reaction mixture was filtered through a fine fritted funnel; the eluent was collected and diluted with 200 mLs of EtOAc. The organic layer was extracted with seven 10 mL portions of H2O and two 15 mL portions of brine. The organic layer was dried with MgSO4 and evaporated to dryness. After purification by flash chromatography 7.8 mmols of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 9.86 (d, J=2.9, 1H), 7.94-7.74 (m, 2H), 7.05-6.92 (m, 2H), 4.02 (td, J=3.1, 6.5, 2H), 1.88-1.73 (m, 2H), 1.44 (dd, J=6.8, 14.2, 2H), 1.39-1.21 (m, 8H), 0.99-0.81 (m, 3H). 13C NMR (126 MHz, CDCl3) δ 190.76, 164.24, 131.95, 129.70, 114.71, 68.40, 31.77, 29.28, 29.03, 25.95, 22.63, 14.08.

Provenance & Evidence