Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 53818886, compound

HRID 1380651Notes

Reaction equation

HRID 1380651 reaction equation
[N+:1]([C:4]1[C:9]([CH:10]=O)=[CH:8][CH:7]=[CH:6][C:5]=1[CH:12]=O)([O-:3])=[O:2].[C:14]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14](=[O:15])[CH:19]=[CH:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:12]=[CH:19][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]=1[N+:1]([O-:3])=[O:2])[CH3:18]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 20194704HCID 20194704, compound

Product 1

HCID 53818886HCID 53818886, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The 2-nitro-1,3-benzenedialdehyde (3.4 g, 0.019 mole) is dissolved in toluene (60 ml) and carbethoxymethylene triphenylphosphorane (19.2 g, 0.06 mole) is added. The mixture is heated at 60° C. for eight hours, cooled, and concentrated at reduced pressure. Diethyl ether (100 ml) is added and the mixture is filtered. The filtrate is concentrated and purified by flash chromatography over silica (elution with 4:1 hexane:ethyl acetate) to afford, after concentration, pure 2-nitro-1,3-benzenediacrylic acid diethyl ester, mp 114°-115° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated at reduced pressure
  3. additionDiethyl ether (100 ml) is added
  4. filtrationthe mixture is filtered
  5. concentrationThe filtrate is concentrated
  6. custompurified by flash chromatography over silica (elution with 4:1 hexane:ethyl acetate)
  7. customto afford
  8. concentrationafter concentration, pure 2-nitro-1,3-benzenediacrylic acid diethyl ester, mp 114°-115° C.

Sources & evidence

ORD record
ord-ea11f09c0a1e468d9ffa25978c3bae15
Source dataset
uspto-grants-1986_04
Patent number
US04582909

Reaction notes

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