Water → Dibenzyl

HRID 541170Notes

Reaction equation

HRID 541170 reaction equation
[C:1]1([C:7]#[C: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.O.C1(/C=C\C2C=CC=CC=2)C=CC=CC=1.C1(/C=C/C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C>[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

6

Reactant 4

HCID 962WaterHCID 10390DiphenylacetyleneHCID 638088trans-StilbeneHCID 5356785cis-Stilbene

Product 1

HCID 7647DibenzylYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.34 g (7.5 mmol) of diphenylacetylene (1), 4.01 mL (225 mmol) of distilled water and stainless steel balls (25 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 6 hours at 650 rpm (reversed every 30 minutes). After the lapse of 6 hours, 200 mL of ethyl acetate was added to the vessel of the ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The filtrate was concentrated, thereby providing reaction products. The confirmation by 1H-NMR thereof revealed that a mixture of cis-1,2-diphenylethylene (26), trans-1,2-diphenylethylene (27) and 1,2-diphenylethane (2) was obtained at a mixing ratio of 92/0/8. The yield was 92%. The reaction is expressed by the following scheme.

Workup

  1. customwas then closed
  2. customfor 6 hours
  3. customto provide a solution
  4. additioncontaining the reaction mixture, which
  5. filtrationwas then filtered with celite
  6. concentrationThe filtrate was concentrated
  7. customproviding
  8. customreaction products

Sources & evidence

ORD record
ord-0815d1501c5a468cb9008937d89b0f0d
Source dataset
uspto-grants-2014_10
Patent number
US08871980B2

Reaction notes

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