Hydroquinone → HCID 53726429, compound

HRID 635831Notes

Reaction equation

HRID 635831 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][CH3:15].[C:16]1([CH:23]=CC(O)=[CH:19][CH:18]=1)O.C=CC=C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:19][CH2:18][CH2:16][CH2:23][C@H:10]2[N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][CH3:15]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 78451,3-ButadieneHCID 7096881,2-Dimethoxy-4-(2-nitrovinyl)benzene

Product 1

HCID 53726429HCID 53726429, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

50.0 g of 3,4-dimethoxy-ω-nitrostyrene and 1.0 g (9.1 mmol) of hydroquinone are suspended in 200 ml of abs. toluene and, at −70° C., admixed with 55.0 g (1.02 mol) of liquid 1,3-butadiene. The mixture is stirred in an autoclave at 160° C. for 6 days and then cooled. Some of the solvent is removed using a rotary evaporator, and the resulting precipitate is filtered off with suction and recrystallized from ethanol. M.p.: 113.5-115.5° C.; Yield 76.3% of Th.

Workup

  1. customat −70° C.
  2. temperaturecooled
  3. customSome of the solvent is removed
  4. customa rotary evaporator
  5. filtrationthe resulting precipitate is filtered off with suction
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-44ada84301f54113b404fe531e5ffc44
Source dataset
uspto-grants-2001_02
Patent number
US06191138B1

Reaction notes

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