4-Nitrobenzoyl chloride → 4-Methyl-4'-nitrobenzophenone

Temperature

0 °C

4-Nitrobenzoyl chloride (5.00 g, 26.0 mmol, 1 eq) was suspended in toluene (10 mL) and the cloudy yellow mixture was cooled to 0° C. in an ice/water bath. Aluminium trichloride (4.50 g, 33.7 mmol, 1.25 eq) was added portionwise over a period of 20 min and the mixture was allowed to warm to room temperature. After stirring at room temperature for 2 hr HPLC indicated that the starting material had been consumed. The reaction was quenched by pouring onto an ice/1 M HCl solution where the product precipitated out as a yellow solid. The aqueous mixture was extracted with ethyl acetate (3×50 mL). The organic washings were dried over magnesium sulfate and concentrated under reduced pressure to give a yellow solid. The yellow solid was recrystallised from 2-propanol to give 4-methyl-4′-nitrobenzophenone (4.05 g, 62% yield) as a yellow crystalline solid.

1. temperatureto warm to room temperature
2. customhad been consumed
3. customThe reaction was quenched
4. additionby pouring onto an ice/1 M HCl solution where the product
5. customprecipitated out as a yellow solid
6. extractionThe aqueous mixture was extracted with ethyl acetate (3×50 mL)
7. dry with materialThe organic washings were dried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customto give a yellow solid
10. customThe yellow solid was recrystallised from 2-propanol

ORD record

ord-56fb12de4b574114a8426f366ca0cea9

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193678B2