Iodine → 1,2-Di-p-tolylethane

200 ml of anhydrous tetrahydrofuran (THF), 3.35 g (0.138 mol) of Mg turnings and a crystal of I2 were placed in a 500-ml three-necked round-bottomed flask equipped with a 100-ml dropping funnel, thermometer and reflux condenser. Then a solution of 35.15 g (0.25 mol) of α-chloro-p-xylene in 50 ml of anhydrous THF was added drop by drop. Heating was required to start the reaction, then self-heating was observed. After 3 hours, all of the Mg had dissolved. The reaction mixture was kept under reflux for 3 hours, then left to rest for one night. All the THF was evaporated at reduced pressure and the residue was treated with a mixture of 150 ml of hexane and 150 ml of 10% HCl. The organic phase was separated, washed with aqueous NaCl (3 times) and dried over Na2SO4. After evaporating the solvent, white crystals were isolated, and these were dried under vacuum at 70° C. 24.3 g of 1,2-di-p-tolylethane was obtained (yield: 92.4%).

1. customequipped with a 100-ml
2. temperaturethermometer and reflux condenser
3. temperatureHeating
4. customthe reaction
5. temperatureself-heating
6. temperatureunder reflux for 3 hours
7. waitleft
8. waitto rest for one night
9. customAll the THF was evaporated at reduced pressure
10. additionthe residue was treated with a mixture of 150 ml of hexane and 150 ml of 10% HCl
11. customThe organic phase was separated
12. washwashed with aqueous NaCl (3 times)
13. dry with materialdried over Na2SO4
14. customAfter evaporating the solvent
15. customwhite crystals were isolated
16. customthese were dried under vacuum at 70° C

ORD record

ord-6ef6969c4f7141b4b7b259668e32ef0b

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369254B1