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

HRID 2897

Reaction equation

HRID 2897 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[Cl: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[Cl:12])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 855054-Chloro-3-nitrobenzaldehydeHCID 178418302HCID 178418302, compound

Product 1

HCID 10760270(Z)-1-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)etheneYield 50.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent2×

Procedure

1.0 g of 3-nitro-4-chlorobenzaldehyde and 2.8 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 50 ml of benzene, and a benzene solution containing 260 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 0.95 g of the intended compound. The yield of the product was 50.4%.

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-7682e2cee87a4592adfa5b6aefdb5c2b
Source dataset
uspto-grants-1998_03
Patent number
US05731353

Linked notes

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