1,3-Butadiene → HCID 69829552, compound

HRID 411850Notes

Reaction equation

HRID 411850 reaction equation
[CH3:1][O:2][CH:3]([O:10][CH3:11])[CH2:4][CH:5]=[CH:6][N+:7]([O-:9])=[O:8].[CH2:12]=[CH:13][CH:14]=[CH2:15]>C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C1(C)C=CC=CC=1>[CH3:11][O:10][CH:3]([O:2][CH3:1])[CH2:4][C@H:5]1[C@H:6]([N+:7]([O-:9])=[O:8])[CH2:15][CH:14]=[CH:13][CH2:12]1

Participants

5

Reactant 2

HCID 78451,3-ButadieneHCID 53757146HCID 53757146, compound

Product 1

HCID 69829552HCID 69829552, compoundYield 125.4%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 1140TolueneSolvent

Procedure

214 g (1.0 mole) 75% 4,4-dimethoxy-1-nitro-1-butene and 0.1 g phenothiazine were put in an autoclave at room temperature, together with 850 ml toluene. Then 216 g (4.0 mole) butadiene were added under pressure. Subsequently stirring was conducted under the own pressure (approx. 6 bar) for 30 hours at 100° C. The pressure was released and the temperature reduced. Finally toluene and unreacted butadiene were distilled off. 270 g of an oily residue were obtained, containing about 39% reaction product and about 10% educt, as confirmed by GC. The crude product was employed without any further purification in the next step.

Workup

  1. distillationFinally toluene and unreacted butadiene were distilled off

Sources & evidence

ORD record
ord-e1b793a1d4854bc297e42f34da47762b
Source dataset
uspto-grants-2003_05
Patent number
US06559318B1

Reaction notes

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