Benzene → Dibenzyl

HRID 358318

Reaction equation

HRID 358318 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)=O.C(O)C.C1C=CC=CC=1>[Pd].O>[C:1]1([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 284Formic AcidHCID 702EthanolHCID 11502Stilbene

Product 1

HCID 7647DibenzylYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a dry, nitrogen-filled 250 ml single-necked round-bottom flask fitted with a nitrogen inlet and magnetic stirring bar was added 11.8 g (65.5 mmol) of stilbene, 11 g (240 mmol) formic acid, 5 g of 10% Pd on activated carbon (4.7 mmol Pd), 60 ml of absolute ethanol and 100 ml of dry benzene. The reaction vessel was placed in a sonicator so that the liquid level inside the flask matched that of the bath water and in the location that produced the maximum cavitation in the flask. After 1 h the flask was removed and the contents filtered. The solid was washed with chloroform and the combined filtrates concentrated on a rotary evaporator. The residual soild was recrystallized (ethanol-pentane) to give 11.03g (92.5% yield) of bibenzyl mp 51°-51.5° (lit 52.5) (8).

Workup

  1. additionTo a dry, nitrogen-filled 250 ml single-necked round-bottom flask
  2. customfitted with a nitrogen inlet and magnetic stirring bar
  3. customproduced the maximum cavitation in the flask
  4. customAfter 1 h the flask was removed
  5. filtrationthe contents filtered
  6. washThe solid was washed with chloroform
  7. concentrationthe combined filtrates concentrated on a rotary evaporator
  8. customThe residual soild was recrystallized (ethanol-pentane)

Sources & evidence

ORD record
ord-40f363345bb14156a5e6e204c259faf9
Source dataset
uspto-grants-1984_08
Patent number
US04466870

Linked notes

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