Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-hydroxy-4-methoxybenzaldehyde (140 g; 0.92 mol) in dimethylformamide (700 ml) was added dry potassium carbonate (2.54 g; 1.84 mol). The mixture was neared to 55° C. and cyclopentyl bromide (74 g; 1.97 ml; 1.84 mol) in dimethylformamide (300 ml) was added dropwise over 2 hours. After complete addition, the mixture was stirred at 55° C. for 15 hours, cooled, filtered and the solvent removed in vacuo. The residue was dissolved in CH2Cl2 and washed with 1.0M NaOH to eliminate any trace of phenol. The organic layer was dried (MgSO4) and purified by column chromatography (SiO2 ; CH2Cl2). The solution was concentrated in vacuo to give the title compound as an oil (192 g). δH (CDCl3) 1.5-2.0 (8H, br m, (CH2)4), 3,87 (3H, s, OMe), 4.80 (1H, br m, OCHCH2), 6.90 (1H, d, J 8.7 Hz, ArH ortho to OMe), 7.30-7.45 (2H, m, 2×ArH meta to OMe) and 9.77 (1H. s, ArCHO)

Provenance & Evidence