Sodium Hydroxide → (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid

HRID 1110515Notes

Reaction equation

HRID 1110515 reaction equation
C([O:3][C:4](=[O:27])/[CH:5]=[CH:6]/[CH:7]=[C:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)C.[OH-].[Na+]>O>[N+:15]([C:11]1[CH:10]=[C:9]([C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[CH:7]/[CH:6]=[CH:5]/[C:4]([OH:27])=[O:3])[CH:14]=[CH:13][CH:12]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14347249(E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347259(E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid ethyl ester (6.1 g) methanol (25 mL) and 2N sodium hydroxide solution (12.5 mL) was stirred at reflux for 15 minutes, then was diluted with water (50 mL) and concentrated in vacuo to remove the methanol. The basic solution was poured into a mixture of ice and 2N hydrochloric acid (20 mL), and the resulting buff-colored solids were filtered and dried to afford 5,5 g of (E)-5,5-bis(3-nitrophenyl)-2,4-pentadienoic acid mp 234°-237° C. Recrystallization of a portion from chloroform-ethanol furnished the acid as its 0.25 molar hydrate, mp 237°-238° C. Anal. Calculated for C17H12N2O6.0.25H2O:C, 59.22; H, 3.65; N, 8.12 Found: C, 59.27; H, 3.63; N, 8.13.

Workup

  1. temperatureat reflux for 15 minutes
  2. concentrationconcentrated in vacuo
  3. customto remove the methanol
  4. additionThe basic solution was poured into a mixture of ice and 2N hydrochloric acid (20 mL)
  5. filtrationthe resulting buff-colored solids were filtered
  6. customdried

Sources & evidence

ORD record
ord-4752bb146f364aacb17ade4f9e537c20
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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