Hydroquinone → HCID 67134284, compound

HRID 534707Notes

Reaction equation

HRID 534707 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[F:5][C:6]1[CH:7]=[C:8]([CH:14]=[C:15]([F:18])[C:16]=1[F:17])[CH:9]=[CH:10][N+:11]([O-:13])=[O:12].C1(C=CC(O)=CC=1)O>C1(C)C=CC=CC=1>[F:5][C:6]1[CH:7]=[C:8]([CH:9]2[CH:10]([N+:11]([O-:13])=[O:12])[CH2:4][CH:3]=[CH:2][CH2:1]2)[CH:14]=[C:15]([F:18])[C:16]=1[F:17]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 78451,3-ButadieneHCID 67134126HCID 67134126, compound

Product 1

HCID 67134284HCID 67134284, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.24 g (60 mmol) of butadiene were condensed at −78° C. into an autoclave under a nitrogen atmosphere. 2.03 g (10 mmol) of 3,4,5-trifluoro-β-nitrostyrene from example 2.2 dissolved in 6 ml of toluene and 30 mg of hydroquinone were added. A nitrogen atmosphere was applied (120 bar) and the suspension was heated for 12 h to 130° C. The reaction mixture was expanded and all volatiles were evaporated in vacuo. Column chromatography (SiO2, cyclohexane/ethylacetate 9:1) yielded 2.4 g (9.4 mmol, 94% of theory) of the title compound as yellowish crystals.

Workup

  1. customcondensed at −78° C. into an autoclave under a nitrogen atmosphere
  2. temperaturethe suspension was heated for 12 h to 130° C
  3. customall volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-a7d5502a7a9247db83f59d688307b443
Source dataset
uspto-grants-2014_10
Patent number
US08853455B2

Reaction notes

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