Hexane → 4-(1-Naphthoyl)-3,5-dichlorotoluene

Temperatur

-60 °C

To a stirred, cold (-60° C.) solution of 3,5-dichlorotoluene (3.5 g, 21.7 mmol) in dry tetrahydrofuran (30 ml), 2.6 M n-butyllithium in hexane (8.78 ml, 22.8 mmol) was added dropwise over 15 minutes. The reaction mixture was stirred for one hour at -60° C. and then treated with a solution of 1-naphthoyl chloride (4.14 g, 21.7 mmol) in 15 ml of dry tetrahydrofuran over a period of 15 minutes. The mixture was stirred for 3.5 hours at -60° C. and then quenched with 4.8 ml of saturated NH4Cl solution. The mixture was permitted to warm to room temperature and then diluted with 30 ml of water and 30 ml of ether. The layers were thoroughly mixed and then separated. The etheral layer was backed-washed with brine and dried with anhydrous magnesium sulfate. Concentration afforded 7.12 g of crude product which was chromatographed on silica gel (20:1 hexane:ethyl acetate) to give 1.59 g (23 %).

1. stirringThe mixture was stirred for 3.5 hours at -60° C.
2. customquenched with 4.8 ml of saturated NH4Cl solution
3. temperatureto warm to room temperature
4. additiondiluted with 30 ml of water and 30 ml of ether
5. additionThe layers were thoroughly mixed
6. customseparated
7. washThe etheral layer was backed-washed with brine
8. dry with materialdried with anhydrous magnesium sulfate
9. concentrationConcentration

ORD-Eintrag

ord-f97f253af5084068965eced3708b300f

Quelldatensatz

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04923885