Sodium Hydroxide → HCID 14347268, compound

HRID 2232810Notes

Reaction equation

HRID 2232810 reaction equation
C[O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[CH:6]=[C:7](\[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[OH-].[Na+]>CO>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14](/[C:7](/[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6]\[CH:5]=[CH:4]\[C:3]([OH:22])=[O:2])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14347270HCID 14347270, compound

Product 1

HCID 14347268HCID 14347268, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the manner described in Example 99, (E,E)-5-(4-methoxyphenyl)-5-(3-pyridinyl)-2,4-pentadienoic acid methyl ester (0.295 g) was saponified in a refluxing mixture of methanol (1.5 mL) and 1N NaOH 1.5 mL). After the cooled reaction was neutralized with 1N HCI (1.5 mL), the crude acid was filtered off and crystallized from methanol to afford 0.235 g of (E,E)-5-(4-methoxyphenyl)-5-(3-pyridinyl)-2,4-pentadienoic acid as its 0.33 molar hydrate, mp 173°-175° C. Anal. Calcd for C17H15NO3 0.33 H2O: C, 71.08: H, 5.49:, N, 4.88. Found: C, 71.01: H, 5.59: N, 4.85.

Workup

  1. customAfter the cooled reaction
  2. filtrationthe crude acid was filtered off
  3. customcrystallized from methanol

Sources & evidence

ORD record
ord-6611a9438e584963ae4b6ab5e4c1fec9
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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