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

HRID 2232763Notes

Reaction equation

HRID 2232763 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 acid

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 5,5g 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.

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-76eb824d6ac74c39a51310a8a2023512
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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