Hydrazine hydrate (1:1) → 1,4-Dibenzylbenzene

HRID 613586Notes

Reaction equation

HRID 613586 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]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 763951,4-Dibenzoylbenzene

Product 1

HCID 2360471,4-DibenzylbenzeneYield 97.4%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

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).

Workup

  1. customIn a 4 neck, 1 liter flask fitted with thermocouple, mechanical stirrer, Barrett trap with condenser
  2. temperatureThe mixture was then heated to 150° C.
  3. customwhile collecting water and excess hydrazine hydrate in the Barrett trap
  4. additionPotassium hydroxide (54.1 g) was slowly added over 0.5 hour while the temperature
  5. temperaturewas slowly increased to 200° C
  6. temperatureThe temperature was maintained at 200° C. for 1 hour
  7. temperatureThe reaction was cooled to 80° C.
  8. additionpoured into 500 ml water
  9. washThe reactor was rinsed with an additional 550 ml water
  10. extractionThe water was extracted 3 times with 250 ml dichloromethane
  11. washthe combined organic phases were washed with 500 ml water
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-895b1b71e6444cdba1a0efd723905ae1
Source dataset
uspto-grants-1999_12
Patent number
US06008283

Reaction notes

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