1,2-Dichlorobenzene → HCID 65449687, compound

Temperature

0 °C

In a dry 250 ml three-neck flask with thermometer, reflux condenser (under nitrogen) and dropping funnel, 17.73 g of AlCl3 (0.133 mol) were suspended in 50 ml of 1,2-dichlorobenzene and cooled to 0° C. While stirring vigorously, 31.6 ml of lauroyl chloride (0.133 mol) were slowly added dropwise (1 hour). The mixture was then allowed to cool until the temperature had reached room temperature. Subsequently, the mixture was heated gradually to approximately 100-105° C., in the course of which a change in colour was evident (from ochre to dark red). Subsequently, the mixture was stirred at this temperature for 5 hours and left to stand overnight at room temperature. To separate the complex, this mixture was cautiously poured onto 200 g of ice (5% HCl) while stirring. The mixture became a mustard-coloured paste which was extracted in ethyl acetate. The organic layer was then removed in a separating funnel and washed to neutrality with saturated sodium hydrogencarbonate solution (2×50 ml) and water. After drying over sodium sulphate, the ethyl acetate was evaporated off. The remaining 1,2-dichlorobenzene was distilled off under reduced pressure. The residue was chromatographed through a column (length=20 cm, diameter=5 cm) on silica gel (Merck 0.040-0.063 nm) with dichloromethane as the eluent.

1. temperatureIn a dry 250 ml three-neck flask with thermometer, reflux condenser (under nitrogen)
2. temperatureto cool until the temperature
3. customhad reached room temperature
4. temperatureSubsequently, the mixture was heated gradually to approximately 100-105° C., in the course of which a change in colour
5. stirringSubsequently, the mixture was stirred at this temperature for 5 hours
6. waitleft
7. customTo separate the complex
8. additionthis mixture was cautiously poured onto 200 g of ice (5% HCl)
9. stirringwhile stirring
10. extractionwas extracted in ethyl acetate
11. customThe organic layer was then removed in a separating funnel
12. washwashed
13. dry with materialAfter drying over sodium sulphate
14. customthe ethyl acetate was evaporated off
15. distillationThe remaining 1,2-dichlorobenzene was distilled off under reduced pressure
16. customThe residue was chromatographed through a column (length=20 cm, diameter=5 cm) on silica gel (Merck 0.040-0.063 nm) with dichloromethane as the eluent

ORD record

ord-c02c0315bc3a43dd9fa4248fbdf8405d

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198433B2