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

HRID 1110505Notes

Reaction equation

HRID 1110505 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. Anal. Calculated for C19H18O4 : C, 73.53; H, 5.85 Found: C, 73.80; H, 5.94

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-2993cf5566714c3fb6ccd116b9f6e2a7
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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