Allylbenzene → 1,1'-(But-2-ene-1,4-diyl)dibenzene

HRID 1811657Notes

Reaction equation

HRID 1811657 reaction equation
C(C1C=CC=CC=1)C=C.[C:10]1([CH2:16]/[CH:17]=[CH:18]\[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([CH2:16][CH:17]=[CH:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 9309AllylbenzeneHCID 122499081,1′-(2Z)-2-Butene-1,4-diylbis[benzene]

Product 1

HCID 5187951,1'-(But-2-ene-1,4-diyl)dibenzene

Procedure

After the reaction was cooled to room temperature, the product was purified by silica column chromatography using hexanes as the eluant. The fraction containing the product was dried via rotavap to remove the solvent, affording the product as colorless liquid. The scale of a typical reaction was 2 mL of the substrate, allyl benzene. (Z)-1,4-diphenylbut-2-ene: 1H NMR (500 MHz, CDCl3) δ 7.30 (m, 10, Ar—H), 5.76 (m, 2, CH), 3.57 (d, 4, CH2, JHH=6 Hz); 13C NMR (125 MHz, CDCl3) δ 141.03, 129.31, 138.73, 128.63, 126.22, 33.74.

Workup

  1. customthe product was purified by silica column chromatography
  2. additionThe fraction containing the product
  3. customwas dried via rotavap
  4. customto remove the solvent
  5. customaffording the product as colorless liquid
  6. customThe scale of a typical reaction

Sources & evidence

ORD record
ord-8b51af7672b84e978c1b4f6f3652e729
Source dataset
uspto-grants-2013_01
Patent number
US08362311B2

Reaction notes

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