Reaction #56199

Reaction equation

methyl indane-2-carboxylate

benzoyl chloride

aluminum chloride

water

aluminum chloride

→

Methyl 5-benzoyl-indan-2-carboxylate

Solvents

methylene chloride

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   OtherIn a 250 cm3 reaction vessel
2. 2
   Otherfitted with a stirrer
3. 3
   workup.ADDITIONis then slowly added at ambient temperature
4. 4
   TemperatureThe mixture is cooled
5. 5
   Otherclose to 20° C.
6. 6
   workup.ADDITIONis added
7. 7
   workup.ADDITIONThe temperature gradually rises during the course of the addition
8. 8
   Temperatureis then heated
9. 9
   Temperatureto reflux for 3 hours
10. 10
    TemperatureAfter cooling
11. 11
    workup.ADDITIONthe mixture is poured
12. 12
    Extractionthe resulting mixture is extracted with chloroform
13. 13
    ExtractionThe chloroform extract
14. 14
    Washis then washed with water
15. 15
    workup.ADDITIONcontaining caustic soda
16. 16
    DryingIt is dried over anhydrous sodium sulphate
17. 17
    FiltrationThe product is then filtered
18. 18
    Concentrationthe filtrate concentrated to an oily residue which
19. 19
    workup.DISTILLATIONis distilled
20. 20
    Othera fraction is collected boiling at 178°-184° C. at 0.6 to 0.8 torr

Procedure

In a 250 cm3 reaction vessel fitted with a stirrer, a cooler, a dropping funnel and a thermometer, is placed 23.2 g (0.173 mole) of anhydrous aluminum chloride in suspension in 40 ml of methylene chloride. 35.3 g (0.252 mole) of benzoyl chloride dissolved in 40 cm3 of methylene chloride is then slowly added at ambient temperature. The aluminum chloride tends to pass into solution while the temperature gradually rises several degrees. The mixture is cooled to hold the temperature close to 20° C. and a solution of 11.1 g (0.063 mole) of methyl indane-2-carboxylate dissolved in 50 cm3 of methylene chloride is added. The temperature gradually rises during the course of the addition and the mixture turns a light brown color. The mixture is stirred for one hour at ambient temperature and is then heated to reflux for 3 hours. After cooling, the mixture is poured into acidified iced water and the resulting mixture is extracted with chloroform. The chloroform extract is then washed with water containing caustic soda, then with slightly acidified water and finally with water. It is dried over anhydrous sodium sulphate. The product is then filtered and the filtrate concentrated to an oily residue which is distilled and a fraction is collected boiling at 178°-184° C. at 0.6 to 0.8 torr.

Source