Sodium Hydroxide → HCID 14347280, compound

HRID 1110566Notes

Reaction equation

HRID 1110566 reaction equation
C[O:2][C:3](=[O:19])/[CH:4]=[CH:5]/[CH:6]=[C:7](\[CH:16]1[CH2:18][CH2:17]1)/[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[OH-].[Na+]>CO>[CH:16]1(/[C:7](/[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:6]\[CH:5]=[CH:4]\[C:3]([OH:19])=[O:2])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86742573HCID 86742573, compound

Product 1

HCID 14347280HCID 14347280, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As described in Example 99, (E,E)-5-cyclopropyl-5-(4-methoxyphenyl)-2,4-pentadienoic acid methyl ester (6.8 g) was saponified in a refluxing mixture of methanol (30 mL) and 2N NaOH (30 mL). After 2.5 hours the cooled reaction was worked up in the usual manner, and the crude acid was crystallized from 2-propanol-hexane to give 5.6 g of (E,E)-5-cyclopropyl-5-(4-methoxyphenyl)-2,4-pentadienoic acid, mp 158°-160° C.

Workup

  1. customAfter 2.5 hours the cooled reaction
  2. customthe crude acid was crystallized from 2-propanol-hexane

Sources & evidence

ORD record
ord-9b047113019b44b59ca45693e05e41a3
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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