Sodium Chloride → (Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene

HRID 2898Notes

Reaction equation

HRID 2898 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH:7]=O)([O-:3])=[O:2].[Br-].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:39]=[C:40]([O:44][CH3:45])[C:41]=1[O:42][CH3:43])[CH2:19]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[Cl-].[Na+]>C1C=CC=CC=1.C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[CH:19]\[C:18]2[CH:39]=[C:40]([O:44][CH3:45])[C:41]([O:42][CH3:43])=[C:16]([O:15][CH3:14])[CH:17]=2)[CH:9]=[CH:10][C:11]=1[CH3:12])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 17989983-Nitro-p-tolualdehydeHCID 178418302HCID 178418302, compound

Product 1

HCID 10711415(Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)etheneYield 49.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent2×

Procedure

1.0 g of 3-nitro-4-methylbenzaldehyde and 3.3 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 50 ml of benzene, and a benzene solution containing 302 mg of sodium hydride dispersed therein was added thereto and reacted for 15 hours at room temperature. The reaction liquid was neutralized with acetic acid, saturated sodium chloride solution was added thereto, and the resulting liquid was extracted with dichloromethane. The extract was dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (diethyl ether:hexane=1:2 by volume) to obtain 0.99 g of the intended compound. The yield of the product was 47.8%.

Workup

  1. additiondispersed
  2. additiontherein was added
  3. customreacted for 15 hours at room temperature
  4. customThe reaction liquid
  5. additionwas added
  6. extractionthe resulting liquid was extracted with dichloromethane
  7. dry with materialThe extract was dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (diethyl ether:hexane=1:2 by volume)

Sources & evidence

ORD record
ord-d94aaed8109c4f10b8798228c27f900e
Source dataset
uspto-grants-1998_03
Patent number
US05731353

Reaction notes

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