HCID 11778959, compound → HCID 67215700, compound

HRID 1190772Notes

Reaction equation

HRID 1190772 reaction equation
S(CCC[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:33]#[N:34])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25]CCCS([O-])(=O)=O)=[CH:21][CH:20]=2)[C:17]#[N:18])=[CH:11][CH:10]=1)([O-])(=O)=O.[Na+].[Na+].COC1C=CC(/C(=C(/C2C=CC(OC)=CC=2)\C#N)/C#N)=CC=1>>[OH:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](=[C:16](/[C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)\[C:17]#[N:18])/[C:33]#[N:34])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 11778959HCID 11778959, compoundHCID 86667407HCID 86667407, compound

Product 1

HCID 67215700HCID 67215700, compound

Procedure

To prepare sodium 1,2-bis[4-(3-sulfonatopropoxyl)phenyl]-1,2-dicyanoethene (3), (1) (0.2903 g, 1 mmol) was dissolved in 10 mL distilled DCM under N2 atmosphere in a 50 mL two-valves round bottom flask. Boron trifluoride methyl sulfide complex (5.26 mL, 50 mmol) was added into the solution slowly. The resulting mixture was stirred at ambient temperature overnight. The solution was concentrated under a stream of N2 and partitioned between 1M HCl and ethyl acetate. The combined organic later were washed with H2O and brine, dried over Na2SO4 and concentrated to give 2,3-bis(4-hydroxyphenyl)fumaronitrile (2) without further purification.

Workup

  1. dissolutionwas dissolved in 10 mL
  2. distillationdistilled DCM under N2 atmosphere in a 50 mL two-valves round bottom flask
  3. additionBoron trifluoride methyl sulfide complex (5.26 mL, 50 mmol) was added into the solution slowly
  4. concentrationThe solution was concentrated under a stream of N2
  5. custompartitioned between 1M HCl and ethyl acetate
  6. washThe combined organic later were washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-00c887d16fea46f9b80d8bbcbadd7f57
Source dataset
uspto-grants-2014_03
Patent number
US08679738B2

Reaction notes

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