Benzene → 1,3-Dibenzoylpropane

A solution of glutaryl chloride (10 mmol, 1.3 mL) dissolved in anhydrous dichloromethane (20 mL) is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere. Aluminum chloride (30 mmol, 4.00 g) is added to the mixture, which immediately turns orange-yellow. A solution of benzene (20 mmol, 1.8 mL) dissolved in anhydrous dichloromethane (10 mL) is added dropwise at room temperature. The solution becomes bright red. The mixture is then refluxed for 24 hours, and turns brown-black. The mixture is then cooled to room temperature and poured into a crystallizing basin containing 20 mL of 10% acidified water, with stirring. A black solid forms, and is filtered off on a Büchner funnel. The yellow organic phase is then extracted with ethyl acetate, dried over MgSO4, filtered, concentrated on a rotary evaporator and recrystallized from 20 mL of methanol. The product obtained is a white solid in a mass of 680 mg. The reaction yield is 27%.

1. additionis introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere
2. additionis added dropwise at room temperature
3. temperatureThe mixture is then refluxed for 24 hours
4. additionpoured into a crystallizing basin
5. additioncontaining 20 mL of 10%
6. filtrationA black solid forms, and is filtered off on a Büchner funnel
7. extractionThe yellow organic phase is then extracted with ethyl acetate
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated on a rotary evaporator
11. customrecrystallized from 20 mL of methanol
12. customThe product obtained
13. customThe reaction yield is 27%

ORD-Eintrag

ord-cd361056b74a4b779691daf7c3b3f2f3

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08383931B2