Hydrazine hydrate (1:1) → Benzene, bis(phenylmethyl)-

HRID 613587Notes

Reaction equation

HRID 613587 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[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:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=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 77388Methanone, 1,3-phenylenebis[phenyl-

Product 1

HCID 121648Benzene, bis(phenylmethyl)-Yield 94.7%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

In a 4 neck, 1 liter flask fitted with thermocouple, mechanical stirrer, Barrett trap with condenser, nitrogen line, and stopper, 1,3-dibenzoylbenzene (197 g) and hydrazine monohydrate (280 g) were heated in diethyleneglycol (540 ml) at 100° C. for 4 hours. The mixture was then heated to 160° C. while collecting water and excess hydrazine hydrate in a Barrett trap. Potassium hydroxide (43.7 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 room temperature and 1 L of water was added and stirred for 20 minutes. The contents were transferred to a separatory funnel. The reactor was rinsed with 250 ml dichloromethane and the rinse added to the water layer. The water was extracted three times with dichloromethane (250 ml each) and the combined organic phases were backwashed with 1 L water. The organic phases were dried over magnesium sulfate, filtered and the solvent removed on a rotary evaporator to give 1,3-dibenzylbenzene as a pale yellow liquid (168.3 g, 94.7% yield).

Workup

  1. customIn a 4 neck, 1 liter flask fitted with thermocouple, mechanical stirrer, Barrett trap with condenser
  2. customwhile collecting water and excess hydrazine hydrate in a Barrett trap
  3. additionPotassium hydroxide (43.7 g) was slowly added over 0.5 hour while the temperature
  4. temperaturewas slowly increased to 200° C
  5. temperatureThe temperature was maintained at 200° C. for 1 hour
  6. temperatureThe reaction was cooled to room temperature
  7. addition1 L of water was added
  8. customThe contents were transferred to a separatory funnel
  9. washThe reactor was rinsed with 250 ml dichloromethane
  10. additionthe rinse added to the water layer
  11. extractionThe water was extracted three times with dichloromethane (250 ml each)
  12. dry with materialThe organic phases were dried over magnesium sulfate
  13. filtrationfiltered
  14. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-d7f03f848efc42d79df1ba5b6fcd23e6
Source dataset
uspto-grants-1999_12
Patent number
US06008283

Reaction notes

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