Nitromethane → 3,4-Dibenzyloxy-beta-nitrostyrene

HRID 1982215Notes

Reaction equation

HRID 1982215 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])=O.[NH4+].[CH3:30][N+:31]([O-:33])=[O:32]>CC(O)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:12]=[CH:30][N+:31]([O-:33])=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 795263,4-Bis(benzyloxy)benzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 5637763,4-Dibenzyloxy-beta-nitrostyreneYield 74.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 79.5 g (1.25 mol) of 3,4-dibenzyloxybenzaldehyde (11) (available from Aldrich Chemical Co.), 47 g CH3CO2NH4, 47 g CH3NO2, and 400 ml CH3CO2H is refluxed for two hours. The mixture is cooled to 23° C. to precipitate the product. The yellow solid is isolated by filtration, washed with ethanol, and air dried. Recrystallization from CH3CO2H--C2H5OH gives 67.2 g (74.5%) of (12): mp 118°-119° C.

Workup

  1. temperatureis refluxed for two hours
  2. customto precipitate the product
  3. customThe yellow solid is isolated by filtration
  4. washwashed with ethanol, and air
  5. customdried
  6. customRecrystallization from CH3CO2H

Sources & evidence

ORD record
ord-90e2e6929ce84f9aaf07dc2ab3990ef2
Source dataset
uspto-grants-1986_06
Patent number
US04595765

Reaction notes

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