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

HRID 1522937Notes

Reaction equation

HRID 1522937 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-32f86e722a55469c92345b23fc3a06e2
Source dataset
uspto-grants-2015_07
Patent number
US09079173B2

Reaction notes

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