Methyl Acrylate → HCID 23453657, compound

HRID 1277366Notes

Reaction equation

HRID 1277366 reaction equation
[N+:1]([CH:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]2[CH2:16][CH2:17][CH:5]1[CH:6]=[CH:7]2)([O-:3])=[O:2].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].O1CCOCC1>C(O)(C)(C)C>[N+:1]([C:4]1([CH2:20][CH2:19][C:18]([O:22][CH3:23])=[O:21])[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]2[CH2:16][CH2:17][CH:5]1[CH:6]=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7294Methyl Acrylate2×HCID 312751,4-DioxaneHCID 23453739HCID 23453739, compound

Product 1

HCID 23453657HCID 23453657, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Variant B: 0.18 mole of 2-nitro-3-phenyl-bicyclo[2.2.2]-oct-5-ene, 0.18 mole of methyl acrylate and 3.8 ml of Triton B in 50 ml of tert.-butanol and stirred for 24 hours, a further 0.18 mole of methyl acrylate and 70 mlof dioxan are then added and the mixture is heated to the reflux temperature for 24 hours. After cooling, the reaction mixture crystallizes. A little ethanol is added, the mixture is neutralized with 2N hydrochloric acid and the crystal sludge is filtered. Recrystallization of the crystals from isopropanol with the addition of animal charcoal gives crystals of melting point 127°-131° C.

Workup

  1. temperaturethe mixture is heated to the reflux temperature for 24 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture crystallizes
  4. additionA little ethanol is added
  5. filtrationthe crystal sludge is filtered
  6. customRecrystallization of the crystals from isopropanol
  7. additionwith the addition of animal charcoal
  8. customgives crystals of melting point 127°-131° C.

Sources & evidence

ORD record
ord-7db12d63af234c1db5f3de3381db0fdc
Source dataset
uspto-grants-1981_07
Patent number
US04277470

Reaction notes

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