Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

Participants

Reaction Steps

A mixture of 3-hydroxy-4-methoxybenzaldehyde (100 grams (g hereinafter), 0.66 moles (mol hereinafter)), potassium carbonate (100 g, 0.73 mol) and bromocyclopentane (80 miliLiters (mL hereinafter), 0.79 mol) in dimethylformamide (0.5 Liters (L hereinafter)) was heated under an argon atmosphere at 100° Centigrade (C hereinafter). After 22 hours (h hereinafter), additional bromocyclopentane (10 mL, 0.1 mol) and potassium carbonate (20 g, 0.14 mol) were added and heating was continued for 24 h. The mixture was allowed to cool and was filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between ether and aqueous sodium carbonate. The organic extract was washed with aqueous sodium carbonate and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 2:1 hexanes/ether to provide a pale yellow oil (121 g, 84%). Analysis Calc. for C13H16O3 :C 70.89, H 7.32; found: C 70.71, H 7.33.

Provenance & Evidence