Hydrochloric Acid → (2-Methylbutyl)benzene

Temperature

20 °C

To a mixture of the nickel catalyst prepared in step (a) (208 gm, 0.39 mmol), chlorobenzene (135 mmol) and ether (50 ml) was added (+)-2-methylbutyl magnesium bromide (60 mmol), prepared in step (b), in 50 ml ether. The mixture was kept at 0° C., with stirring, over 10 minutes. The resulting mixture was heated to reflux for 20 hr. The reactants were cooled to 20° C. and 10% hydrochloric acid was added to hydrolyze the mixture. Sodium chloride is added to saturate the aqueous layer and the water phase was extracted with 3-50 ml portions of ether. The combined extracts are washed with water, dried over calcium chloride, and concentrated in vacuo. The residue was distilled under reduced pressure and the product, which boiled at 91° C. (25 mm Hg), was collected. The structure of the product was confirmed by NMR.

1. customwas kept at 0° C.
2. temperatureThe resulting mixture was heated
3. temperatureto reflux for 20 hr
4. concentrationto saturate the aqueous layer
5. extractionthe water phase was extracted with 3-50 ml portions of ether
6. washThe combined extracts are washed with water
7. dry with materialdried over calcium chloride
8. concentrationconcentrated in vacuo
9. distillationThe residue was distilled under reduced pressure
10. customthe product, which boiled at 91° C. (25 mm Hg), was collected

ORD record

ord-fa2e8abab12648ef9c54fba110512cb1

Source dataset

uspto-grants-1983_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04394070