(E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester → (E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid

HRID 2232753Notes

Reaction equation

HRID 2232753 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+]>[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

3

Reactant 1

HCID 86742566(E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347241(E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acidYield 87.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of (E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester (19.8 g) methanol (200 mL) and 2N sodium hydroxide solution (40 mL) was heated at reflux for 30 minutes. After most of the methanol was distilled off in vacuo, the solution was diluted with water (300 ml), acidified with 2N hydrochloric acid (50 mL) and the resulting solid filtered. The dried material (17.8 g) was crystallized from dichloromethane-hexane to afford 15.9 g of (E)-5,5-bis (3-methoxyphenyl)-2,4-pentadienoic acid, mp 179°-180.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. distillationAfter most of the methanol was distilled off in vacuo
  4. additionthe solution was diluted with water (300 ml)
  5. filtrationthe resulting solid filtered
  6. customThe dried material (17.8 g) was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-4ffbac5c782849c8a60a9963e369ee86
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

Loading…