Sodium Hydroxide → (Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid

HRID 1110506Notes

Reaction equation

HRID 1110506 reaction equation
C([O:3][C:4](=[O:25])/[CH:5]=[CH:6]\[CH:7]=[C:8]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)C.[OH-].[Na+]>CO>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:7]/[CH:6]=[CH:5]\[C:4]([OH:25])=[O:3])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86742565(Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347242(Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar fashion, (Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester (2.2 g) in methanol (15 mL) was hydrolyzed using 2N sodium hydroxide solution (5 mL). The usual work up furnished 2.0 g of (Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid. Crystallization of a portion from ether furnished the analytically pure acid, mp 178°-180° C. Anal. Calculated for C19H18O4C: 73.53; H, 5.85 Found: C, 73.29; H, 5.91.

Sources & evidence

ORD record
ord-646dd42794e94039b2aef3d5c46aebc0
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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