Dimethylformamide → p-Cyclohexylbenzaldehyde

Temperatur

-78 °C

To a solution of 1-bromo-4-cyclohexylbenzene (850 mg, 3.55 mmol) in THF (4.0 mL) was added n-BuLi (3.1 mL, 4.62 mmol) at −78° C. under an inert atmosphere. The reaction mixture was stirred for 60 min at −78° C., and then DMF (2.8 mL) was added. The reaction mixture was then stirred for an additional hour at −78° C., warmed to 0° C., and quenched with a saturated NH4Cl solution. The mixture was then extracted with ethyl acetate (2×30 mL). The combined organic layers were then dried over magnesium sulfate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-cyclohexylbenzaldehyde (250 mg, 38%) as a solid.

1. stirringThe reaction mixture was then stirred for an additional hour at −78° C.
2. temperaturewarmed to 0° C.
3. customquenched with a saturated NH4Cl solution
4. extractionThe mixture was then extracted with ethyl acetate (2×30 mL)
5. dry with materialThe combined organic layers were then dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto obtain the crude product
9. customThe crude material was purified via silica gel column chromatography

ORD-Eintrag

ord-fd5d4f03234a4af58d408505126654dd

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08481532B2