3-Methyl-4-anisaldehyde → 1-Methoxy-2-methyl-4-[2-(4-nitrophenyl)ethenyl]benzene

HRID 703757Notes

Reaction equation

HRID 703757 reaction equation
[O-]CC.[Na+].[N+:5]([C:8]1[CH:22]=[CH:21][C:11]([CH2:12]P(=O)(OCC)OCC)=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH3:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:27]=O>C(O)C>[CH3:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:12][C:11]2[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:22][CH:21]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 1229363-Methyl-4-anisaldehydeHCID 256065Diethyl 4-nitrobenzylphosphonateHCID 2723922Sodium ethoxide

Product 1

HCID 539600651-Methoxy-2-methyl-4-[2-(4-nitrophenyl)ethenyl]benzeneYield 47.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (prepared from 0.70 g of Na and 30 mL of ethanol) was added to an ice-cold mixture of diethyl p-nitrobenzylphosphonate (9.09 g, 0.033 mole) and 3-methyl-p-anisaldehyde (5.0 g, 0.033 mole) in ethanol (about 100 mL). The resulting mixture was stirred overnight. The solid product was filtered, washed with ethanol and vacuum dried to give MMONS, 3-methyl-4-methoxy-4'-nitrostilbene (4.946 g, 0.0157 mole, 47.6% yield, m.p. 109°-111° C.). Recrystallization of MMONS from chloroform/ethanol gave crystals suitable for x-ray analysis.

Workup

  1. filtrationThe solid product was filtered
  2. washwashed with ethanol and vacuum
  3. customdried

Sources & evidence

ORD record
ord-a4a5c24b24814e31944ce154b7544aab
Source dataset
uspto-grants-1991_01
Patent number
US04985178

Reaction notes

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