Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

Participants

Reaction Steps

Caesium carbonate (214 g, 0.66 mol) was added to a mixture of 3-hydroxy-4-methoxybenzaldehyde (100 g, 0.66 mol) and cyclopentyl bromide (98 g, 0.66 mol) in anhydrous DMF (50 ml). The reaction mixture was stirred at RT for 16 h then treated with a further portion of cyclopentyl bromide (98 g, 0.66 mol) and caesium carbonate (214 g, 0.66 mol). After a further 6 h at RT, the mixture was filtered and concentrated in vacuo. The residue was dissolved in dichloromethane (300 ml) and washed with sodium hydroxide solution (10%; 2×150 ml). The organic layer was dried (MgSO4), concentrated in vacuo, and distilled (150° C., 10-2 mbar) to afford the title compound (130 g) as a viscous colourless oil. (Found: C, 70.38; H, 7.48. C13H16O3 requires C, 70.89; H, 7.32%); δH (CDCl3) 1.5-2.0 (8 H, br m, CH2)4), 3.87 (3H, s, OMe), 4.80 (1 H, br m, OCHCH2), 6.90 (1 H, d, J 8.7 Hz, ArH ortho to OMe), 7.30-7.45 (2 H, m, 2×ArH meta to OMe), and 9.77 (1 H, s, ArCHO).

Provenance & Evidence