Thionyl Chloride → 4-chloro-2,3-dihydro-1H-inden-1-one

Temperature

80 °C

33.5 g (181 mmol) of the 1-(2-carboxyethyl)-2-chlorobenzene and 83.4 ml of thionyl chloride are placed in a reaction vessel and stirred at 80° C. for one hour. The excess thionyl chloride is subsequently taken off and the residue is admixed with 200 ml of heptane. The reaction mixture is stirred for 30 minutes and the solvent is subsequently removed in an oil pump vacuum. The residue is taken up in 536 ml of methylene chloride and, while cooling in ice, 48.4 g (363 mmol) of aluminum trichloride are added a little at a time over a period of 10 minutes. The resulting reaction solution is stirred at 0° C. for another 2 hours before the reaction mixture is poured onto 300 ml of ice water. After the aqueous phase has been separated off and extracted once with 60 ml of toluene, the combined organic phases are washed with 80 ml of water and with 100 ml of saturated NaCl solution. After drying over magnesium sulfate, the solvent is removed in an oil pump vacuum. 29 g (96%) of the desired product are isolated.

1. stirringThe reaction mixture is stirred for 30 minutes
2. customthe solvent is subsequently removed in an oil pump vacuum
3. temperaturewhile cooling in ice
4. customThe resulting reaction solution
5. stirringis stirred at 0° C. for another 2 hours before the reaction mixture
6. customAfter the aqueous phase has been separated off
7. extractionextracted once with 60 ml of toluene
8. washthe combined organic phases are washed with 80 ml of water and with 100 ml of saturated NaCl solution
9. dry with materialAfter drying over magnesium sulfate
10. customthe solvent is removed in an oil pump vacuum

ORD record

ord-22c45a0048a14569a1afb2f9294c9f15

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627764B1