Water → 1-(1-Propenyl)spiro[2.4]heptan-4-one

2.1 g (25 mM) of cyclopentanone, containing 0.3% of water, in 20 ml of THF were added dropwise to the reaction mixture while stirring. After having been left for two supplemental hours at reflux and stirring, the reaction mixture was cooled to room temperature, poured onto ice and extracted with ether. The combined organic extracts were successively washed with 1N HCl, a diluted aqueous solution of sodium bicarbonate and finally water. By the evaporation of the volatile components there were obtained 3.7 g of residue which, upon bulb-distillation gave 2.25 g (yield 67%) of the desired spiro-heptanone having a b.p. of 110°-125°/10 Torr. The assessed purity is of about 90%. The product represents an isomeric mixture containing cis- and trans- 1-(prop-1-en-1-yl) spiro [2.4]heptan-4-one in a 2:1 respective weight ratio.

1. waitAfter having been left for two supplemental hours
2. temperatureat reflux
3. stirringstirring
4. additionpoured onto ice
5. extractionextracted with ether
6. washThe combined organic extracts were successively washed with 1N HCl
7. customBy the evaporation of the volatile components

ORD record

ord-d49c75720fea49fe90fb4ef68aa5e2db

Source dataset

uspto-grants-1979_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04176139