Hydrochloric Acid → 1,1-Cyclopropanediethanol

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).

1. temperatureafter cooling again to −10° C.
2. filtrationfiltered off with suction through Celite
3. washThe residue was washed with ethyl acetate and water
4. extractionextracted repeatedly with ethyl acetate
5. dry with materialThe combined organic phases were dried over sodium sulphate
6. concentrationconcentrated under reduced pressure
7. customThe residue was recrystallized from acetonitrile

ORD record

ord-d9d26950ab8446658f7cb11c9a81120a

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309198B2