Sodium Hydroxide → HCID 14347269, compound

HRID 2232811Notes

Reaction equation

HRID 2232811 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 14347271HCID 14347271, compound

Product 1

HCID 14347269HCID 14347269, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the manner described in Example 99, (2E,4Z)-5-(4-methoxyphenyl)-5-(3-pyridinyl)-2,4-pentadienoic acid methyl ester (6.2 g) was saponified a refluxing mixture of methanol (30 mL) and 1N NaOH (30 mL). After 1 hour, the cooled reaction was neutralized with the addition of 1N HCI (30 mL) and the resulting crystalline solid was filtered off and washed well with water to give 5.8 g of (2E,4Z)-5-(4-methoxyphenyl)-5(3-pyridinyl)-2,4-pentadienoic acid, mp 235°-238° C. A sample was recrystallized from methanol to furnish the analytical specimen, mp 238°-240° C.

Workup

  1. customthe cooled reaction
  2. additionwas neutralized with the addition of 1N HCI (30 mL)
  3. filtrationthe resulting crystalline solid was filtered off
  4. washwashed well with water

Sources & evidence

ORD record
ord-1f39b8bc2de34e3587479e37939b9769
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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