Hydrazine hydrate (1:1) → 1,4-Dibenzylbenzene
Reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)COCCO>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
In a 4 neck, 1 liter flask fitted with thermocouple, mechanical stirrer, Barrett trap with condenser, nitrogen line, and stopper, was added 1,4-dibenzoylbenzene (90.5 g), hydrazine monohydrate (172.4 g) and diethyleneglycol (400 ml). The reaction mixture was heated at 100° C. for 1.5 hours. The mixture was then heated to 150° C. while collecting water and excess hydrazine hydrate in the Barrett trap. Potassium hydroxide (54.1 g) was slowly added over 0.5 hour while the temperature was slowly increased to 200° C. The temperature was maintained at 200° C. for 1 hour. The reaction was cooled to 80° C. and then poured into 500 ml water. The reactor was rinsed with an additional 550 ml water and combined with the quench solution. The water was extracted 3 times with 250 ml dichloromethane, the combined organic phases were washed with 500 ml water, dried over magnesium sulfate, filtered and the solvent removed on a rotary evaporator to give 1,4-dibenzylbenzene as a white solid (79.5 g, 97.4% yield).