Hydroquinone → (Tetrachloro-1,4-phenylene)bismethylene diacrylate

HRID 1439425Notes

Reaction equation

HRID 1439425 reaction equation
[C:1](=[O:4])([O-:3])[O-].[Na+].[Na+].N#N.[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].[C:14]1(C=CC(O)=C[CH:16]=1)O.[Cl:22][C:23]1[C:28]([CH2:29]Cl)=[C:27]([Cl:31])[C:26]([Cl:32])=[C:25]([CH2:33]Cl)[C:24]=1[Cl:35]>CN(C)C=O.O>[C:1]([O:3][CH2:29][C:28]1[C:23]([Cl:22])=[C:24]([Cl:35])[C:25]([CH2:33][O:12][C:9](=[O:13])[CH:10]=[CH2:11])=[C:26]([Cl:32])[C:27]=1[Cl:31])(=[O:4])[CH:14]=[CH2:16]

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 947NitrogenHCID 6581Acrylic AcidHCID 10340Sodium CarbonateHCID 66179Alpha,alpha',2,3,5,6-hexachloro-4-xylene

Product 1

HCID 94127(Tetrachloro-1,4-phenylene)bismethylene diacrylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

14.7 g of sodium carbonate (0.14 mole) was added portion-wise, with stirring, and under a current of N2, to 20.3 g of acrylic acid (0.28 mole) plus 1 g of hydroquinone in 200 ml of dimethylformamide at 60°. After dissolution had taken place, the solution was heated with 41.7 g of tetrachloro-p-xylylene chloride (0.132 mole) for 1 hour at 120° C. Then 700 ml of water was added; the crystallizate was suction filtered, washed free of NaCl and dried.

Workup

  1. customat 60°
  2. dissolutionAfter dissolution
  3. filtrationfiltered
  4. washwashed free of NaCl
  5. customdried

Sources & evidence

ORD record
ord-8387a69d943f4d7c800d987434f5fd74
Source dataset
uspto-grants-1977_11
Patent number
US04059618

Reaction notes

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