Water → 2-(Chloromethylidene)-3,3-dimethyloxolane

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Reaction Conditions

Reaction Steps

806 g (4 moles) of 1,1,5-trichloro-3,3-dimethyl-1-pentene are heated under reflux with 360 g (4.4 moles) of anhydrous sodium acetate in 1 liter of dimethylformamide for 6 hours. After cooling to about 100° C., 1.6 liters (8 moles) of 30% strength sodium methylate solution in methanol are added dropwise and the mixture is heated under reflux for a further 4 hours. The cold solution is poured into water and extracted several times with methylene chloride. After the solution has been dried and the solvent has been distilled off, 654 g of product remain, and are fractionated over a column. 522 g (80% of theory) of 2-chloromethylene-3,3-dimethyl-tetrahydrofuran of boiling point 84°-87° C./20 mbar are obtained.

Provenance & Evidence