Ethanol → (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid ethyl ester

HRID 1110514Notes

Reaction equation

HRID 1110514 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[CH:11]C=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:23]([CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:25][CH2:26][CH3:27])=[O:24].[CH2:48](O)C>>[CH2:26]([O:25][C:23](=[O:24])/[CH:28]=[CH:48]/[CH:11]=[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:27]

Participants

4

Reactant 3

HCID 702EthanolHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 143472323,3-Bis(3-nitrophenyl)-2-propenal

Product 1

HCID 14347249(E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid ethyl ester

Procedure

As in Example 99, a solution of 3,3-bis(3-nitrophenyl)-2-propenal (7.9 g) and (carboethoxymethylene)triphenylphosphorane (9.75 g) in ethanol was stirred at room temperature for 1 hour. The usual work up gave a mixture of esters which was crystallized from dichloromethane-hexane to furnish 6.7 g of (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid ethyl ester, mp 121°-123° C. Recrystallization from the same solvent gave the analytical sample, mp 122°-123° C. Anal. Calculated for C19H16N2O6 : C, 61.96; H, 4.38; N, 7.60 Found: C, 62.63; H, 4.60; N, 7.79.

Workup

  1. customThe usual work up gave
  2. customwas crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-c10e502f29da4cf7be05f2f47e08f9e2
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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