Hexane → 4-(2-Naphthoyl)-3,5-dichlorotoluene

Temperatur

-60 °C

To a cold (-60° C.) stirred solution of 3,5-dichlorotoluene (2.5 g, 15.5 mmol) in 30 ml of dry tetrahydrofuran under a nitrogen atmosphere, a 2.6 M solution of n-butyllithium in hexane (6.3 ml, 16.3 mmol) was added slowly over 15 minutes. The reaction mixture was stirred for an additional 30 minutes at -60° C. and then treated dropwise with a solution of 2-naphthoyl chloride (2.95 g, 15.5 mmol) in 15 ml of dry tetrahydrofuran over 15 minutes. The reaction mixture was stirred for 4 hours at -60° C. and then quenched with 4 ml of saturated NH4Cl solution. The mixture was permitted to come to room temperature at which point it was diluted with 20 ml of water and 20 ml of ether. The layers were separated and the aqueous layer further extracted with ether. The combined extracts were washed with brine, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give 4.76 g of crude product. This material was chromatographed on silica gel (20:1 hexane:ethyl acetate) to give 1.71 g of pure product.

1. stirringThe reaction mixture was stirred for 4 hours at -60° C.
2. customquenched with 4 ml of saturated NH4Cl solution
3. customto come to room temperature at which point it
4. additionwas diluted with 20 ml of water and 20 ml of ether
5. customThe layers were separated
6. extractionthe aqueous layer further extracted with ether
7. washThe combined extracts were washed with brine
8. dry with materialdried with anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customto give 4.76 g of crude product
11. customThis material was chromatographed on silica gel (20:1 hexane:ethyl acetate)

ORD-Eintrag

ord-d822df5625134a46be293319622d3a8e

Quelldatensatz

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04923885