Toluene → 3-Methyl-indan-1-one

Temperatur

0 °C

As presented in the following reaction formula, a mixture of 3-phenylbutanoic acid (30 g, 0.18 mol) in thionyl chloride (SOCl2; 100 mL) was refluxed under heating for 2 hours, and then the thionyl chloride was removed. Toluene (200 mL) and aluminum chloride (AlCl3; 24 g, 0.18 mol) were added to the resulting mixture at 0° C., and the reaction mixture was stirred at 0° C. for 0.5 hours, followed by refluxing under heating. After the completion of reaction, the mixture was treated with ice water and then extracted twice with 200 mL of dichloromethane (DCM). The combined organic phase was washed with water (100 mL) and saturated brine (100 mL), and dried and concentrated with magnesium sulfate to give a crude product. The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.)) using an eluent of pentane (PE):ethyl acetate (20:1 (by volume)) to give 3-methyl-2,3-dihydro-1H-inden-1-one (16 g, yield: 60%) as a brown oil.

1. temperaturewas refluxed
2. temperatureunder heating for 2 hours
3. customthe thionyl chloride was removed
4. temperatureby refluxing
5. temperatureunder heating
6. customAfter the completion of reaction
7. extractionextracted twice with 200 mL of dichloromethane (DCM)
8. washThe combined organic phase was washed with water (100 mL) and saturated brine (100 mL)
9. customdried
10. concentrationconcentrated with magnesium sulfate
11. customto give a crude product
12. customThe crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.))

ORD-Eintrag

ord-6c97d65c931f49c28c77ce5252eb5b4f

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242928B2