Thionyl Chloride → (1S-trans)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chloride

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Reaction Steps

In a 300 ml flask, there were charged n-pentane (100 ml) and (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid (50.0 g), and thionyl chloride (46.0 g) was added thereto from a dropping funnel in 20 minutes with stirring under reflux. After completion of the addition, stirring was continued for a further 3 hours, and then the solvent and excess of the thionyl chloride were removed by distillation. The residue was distilled to give (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid chloride (53.9 g) having a boiling point of 50° C/0.5 mmHg - 56° C/0.6 mmHg. Other cyclopropanecarboxylic acid halides were prepared in the same manner as above.

Provenance & Evidence