4-Hydroxybenzaldehyde → HCID 86749477, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,8-dibromooctane (8.0 g, 29.5 mmol), p-hydroxy-benzaldehyde (7.2 g, 59 mmol) and potassium carbonate (8.2 g, 6.0 mmol) in DMF (50 ml) was heated to 55° C. with stirring for 8 h. The cooled solution was poured into water and the precipitate was filtered, washed with water, and dried. Recrystallisation from hot ethanol (200 ml) yielded (15) (7.72 g, 73%), m.p. 89° C.-91° C., (Found C. 74.4, H 7.4 %. C22H26O4 requires C 74.5, H 7.4 %), 1H NMR (250.1 MHz, CDCl3) δ: 1.3-1.9(12H, m, alkyl), 4.02(4H, t, J=7 Hz, CH2O), 6.97 and 7.81 (8H, 2 d, J=11 Hz, aromatic), 9.85 (2H, s, CHO); IR (KBr) vmax /cm-1 1698 s, 1598 s, 1156 s, 834 s. m/z 354 (M, 45), 326 (30), 233 (15), 121 (55), 69 (100).

Provenance & Evidence