Hydrochloric Acid → 1,8-Nonadien-5-ol

A 300 ml-capacity three neck flask containing a stirring bar and Mg (8 g, 16.3 mmol) and connected to a condenser was sufficiently dried. Then, a nitrogen atmosphere was established in the flask, and diethyl ether (24.5 ml) and I2 were introduced into the flask. When a solution of 1-bromo-3-butene (7) (22 ml, 16.3 mmol) in diethyl ether (24.5 ml) was slowly added to the brown suspension thus obtained, a reaction started, and a color of I2 disappeared. After generation of a Grignard reagent, HCOOMe (9.78 ml, 16.3 mmol) was slowly dropped into the flask, and the mixture thus obtained was stirred for 30 minutes. Subsequently, when generation of alcohol was recognized by thin-layer chromatography (hexane:ethyl acetate=10:1), diluted hydrochloric acid was added to the mixture to stop the reaction. After cooling the mixture, an organic layer was separated and extracted with ethyl acetate. This organic layer was dehydrated over Na2SO4 and filtered. The solvent was distilled off, and the organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1). Thus, 1,8-nonadiene-5-ol (8) (11.613 g, 8.3 mmol, yield: 51%) was obtained as an intended compound.

1. additionA 300 ml-capacity three neck flask containing a stirring bar
2. customwas sufficiently dried
3. additionwere introduced into the flask
4. customthus obtained
5. customthe mixture thus obtained
6. additionwas added to the mixture
7. customthe reaction
8. temperatureAfter cooling the mixture
9. customan organic layer was separated
10. extractionextracted with ethyl acetate
11. filtrationfiltered
12. distillationThe solvent was distilled off
13. customthe organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1)

ORD record

ord-03eb05208cf04dbb81bb0e15e5342930

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987044B2