Dimethylformamide → 9-Cyclopropylnonanoyl chloride

Participants

Reaction Steps

A mixture of 0.85 g. of 9-cyclopropylnonanoic acid, 0.45 ml. of thionyl chloride (density 1.656) and 0.10 ml. of dimethylformamide (density 0.945) in 10 ml. ether is stirred overnight at room temperature. The upper layer of the reaction mixture is then separated and the solvent removed by evaporation to yield 9-cyclopropylnonanoyl chloride to which is added at 0° under nitrogen 0.474 g. of 1-octanol and 40 ml. of ether. To this mixture is added dropwise 0.52 ml. of pyridine (density 0.98). The reaction mixture is then stirred 1/2 hours at 0° and overnight at room temperature. An additional 0.20 g. of 1-octanol is then added and the reaction mixture is stirred for 1 day. The mixture is filtered, 3 equivalents of water are added and then the mixture is stirred for 1 hour. Ether is added to dilute the reaction mixture which is washed in turn with 2N sulfuric acid (2 × 50 ml.), 10% aqueous sodium carbonate (2 × 50 ml.), water (2 × 50 ml.) saturated aqueous copper sulfate, water (2 × 50 ml.) and saturated aqueous sodium chloride (1 × 50 ml.). The solution is then dried over calcium sulfate and the solvent removed by evaporation to yield 1.14 g. of octyl 9-cyclopropylnonanoate which is purified by preparative thin layer chromotography (15% ether/hexane solvent).

Provenance & Evidence