Acetic Acid → 3,4-Methylenedioxy-beta-nitrostyrene

HRID 2170751Notes

Reaction equation

HRID 2170751 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=2[O:2]1.C([O-])(=O)C.[NH4+].C(O)(=O)C.[N+:21]([CH3:24])([O-:23])=[O:22]>>[N+:21](/[CH:24]=[CH:6]/[C:5]1[CH:8]=[CH:9][C:10]2[O:11][CH2:1][O:2][C:3]=2[CH:4]=1)([O-:23])=[O:22]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 8438PiperonalHCID 517165Ammonium Acetate

Product 1

HCID 6722963,4-Methylenedioxy-beta-nitrostyrene

Conditions

Temperature
70 °C

Procedure

3,4-methylenedioxybenzaldehyde (15.55 Kg) was treated sequentially with ammonium acetate (13.4 Kg,), acetic acid (45.2 Kg) and nitromethane (18.4 Kg), warmed to 70° C., stirred for 30 minutes, warmed to 80° C., stirred for 10 hours, cooled to 10° C. and filtered. The filtrant was washed with acetic acid (2×8 Kg) and water (2×90 Kg) and dried under a nitrogen stream then in under vacuum at 50 ° C. for 2 days.

Workup

  1. temperaturewarmed to 80° C.
  2. stirringstirred for 10 hours
  3. temperaturecooled to 10° C.
  4. filtrationfiltered
  5. washThe filtrant was washed with acetic acid (2×8 Kg) and water (2×90 Kg)
  6. customdried under a nitrogen stream
  7. waitin under vacuum at 50 ° C. for 2 days

Sources & evidence

ORD record
ord-52f606b409cb4932b4a492aa3daba186
Source dataset
uspto-grants-2015_06
Patent number
US09051301B2

Reaction notes

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