Hydroquinone → 3',5'-Dimethoxy-2-nitro-1,2,3,6-tetrahydro-1,1'-biphenyl

HRID 1632576Notes

Reaction equation

HRID 1632576 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)[CH:6]=[CH:7][N+:8]([O-:10])=[O:9].[CH2:16]=[CH:17][CH:18]=[CH2:19].C1(C=CC(O)=CC=1)O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]2[CH:7]([N+:8]([O-:10])=[O:9])[CH2:19][CH:18]=[CH:17][CH2:16]2)[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 78451,3-ButadieneHCID 6106161,3-dimethoxy-5-(2-nitroethenyl)benzene

Product 1

HCID 133666703',5'-Dimethoxy-2-nitro-1,2,3,6-tetrahydro-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

A stainless steel pressure vessel was charged with 28.6 g. (0.137 mole) 3,5-dimethoxy-beta-nitrostyrene, 20 g. (0.378 mole) butadiene, 40 ml. toluene and a few crystals of hydroquinone. The vessel was cooled to -78° C. under a nitrogen atmosphere and sealed. The sealed vessel was heated at 100° C. for 48 hours, cooled and the reaction mixture concentrated under nitrogen. The residual solid was crystallized from methanol to afford 29.8 g. of title compound, M.P. 80.5°-82° C. J. Org. Chem., 27, 376 (1962) reported M.P. 73°-75° C. 1H-NMR (CDCl3) ppm (delta): 3.75 (s, 6H, OCH3), 4.95 (m, 1H, CHNO2), 5.75 (s, 2H, olefin), 6.40 (s, 3H, aromatic).

Workup

  1. additionA stainless steel pressure vessel was charged with 28.6 g
  2. customsealed
  3. temperatureThe sealed vessel was heated at 100° C. for 48 hours
  4. temperaturecooled
  5. concentrationthe reaction mixture concentrated under nitrogen
  6. customThe residual solid was crystallized from methanol
  7. customto afford 29.8 g

Sources & evidence

ORD record
ord-633b2f4075614449895f7a8083f6b5a7
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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