Hydrochloric Acid → 1,1-Cyclopropanediethanol

Participants

Reaction Steps

109.5 g (crude product, about 547 mmol) of ethyl methyl 2,2′-cyclopropane-1,1-diyldiacetate were dissolved in 750 ml of p.a. THF, and, at −20° C., 984 ml (984 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. The reaction mixture was warmed to RT overnight and, after cooling again to −10° C., 500 ml of isopropanol were added carefully. The mixture was acidified with 1 N hydrochloric acid and filtered off with suction through Celite. The residue was washed with ethyl acetate and water. The filtrate was saturated with sodium chloride and extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was recrystallized from acetonitrile. This gave 50.4 g of the target product (70.8% of theory).

Provenance & Evidence