1,3-Butadiene → HCID 68771799, compound

HRID 1172319Notes

Reaction equation

HRID 1172319 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[Cl:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[CH:8]=[CH:9][N+:10]([O-:12])=[O:11]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C@H:8]1[C@H:9]([N+:10]([O-:12])=[O:11])[CH2:4][CH:3]=[CH:2][CH2:1]1

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 98458o-Chloro-beta-nitrostyrene

Product 1

HCID 68771799HCID 68771799, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A 10 mL solution of 1:1 1,3-butadiene and toluene stored at −20° C. and 2-chloro-β-nitrostyrene (2.0 g, 11 mmol) were added to a pressure tube and sealed. The solution was heated to 110° C. and stirred for three days. The reaction mixture was cooled to room temperature, concentrated, and the residue was crystallized from hexanes to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.35-7.38 (m, 1H), 7.15-7.29 (m, 3H), 5.71-5.84 (m, 2H), 5.09-5.16 (m, 1H), 4.04-4.13 (m, 1H), 2.76-2.84 (m, 2H), 2.54-2.60 (m, 1H), 2.19-2.28 (m, 1H).

Workup

  1. customstored at −20° C.
  2. customsealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated
  5. customthe residue was crystallized from hexanes

Sources & evidence

ORD record
ord-3ab06f09a1864851a7c1f80cc1369f9f
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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