Acetic Acid → HCID 15576529, compound

HRID 2249119Notes

Reaction equation

HRID 2249119 reaction equation
[BH4-].[Na+].C(O)C.[N+:6]([CH:9]=[CH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1)([O-:8])=[O:7].C(O)(=O)C>O1CCOCC1>[N+:6]([CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1)([O-:8])=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 6106161,3-dimethoxy-5-(2-nitroethenyl)benzeneHCID 4311764Sodium borohydride

Product 1

HCID 15576529HCID 15576529, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a well stirred suspension of sodium borohydride (5 g) in a mixture of dioxane (100 ml) and absolute ethanol (30 ml) was added dropwise a solution of 1-(2-nitroethenyl)-3,5-dimethoxybenzene (12.6 g) in dioxane (100 ml) over a 1 hour period. Following addition the mixture was stirred for an additionnal 45 minutes period. To the resulting suspension were added ice-water (120 ml) and 50% aqueous acetic acid (10 ml). Agitation was maintained for 1 hour and the clear solution was concentrated under reduced pressure. The residue was extracted with ethyl acetate/water, the organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. Evaporation of solvents afforded the crude title compound (10.8 g). Trap to trap distillation under high vacuum (0.05 Millibars) at 180° C. yielded 1-(2-nitroethyl)-3,5-dimethoxybenzene as a colorless oil (6.8 g).

Workup

  1. additionaddition the mixture
  2. stirringwas stirred for an additionnal 45 minutes period
  3. temperatureAgitation was maintained for 1 hour
  4. concentrationthe clear solution was concentrated under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate/water
  6. washthe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of solvents
  9. customafforded the crude title compound (10.8 g)
  10. distillationTrap to trap distillation under high vacuum (0.05 Millibars) at 180° C.

Sources & evidence

ORD record
ord-3f2f44575d7f48c5a9f85284c9eea486
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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