Potassium Hydroxide → HCID 14347236, compound

HRID 2232742Notes

Reaction equation

HRID 2232742 reaction equation
C([O:3][C:4](=[O:21])/[CH:5]=[CH:6]\[CH:7]=[C:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.[OH-].[K+]>CO>[C:9]1([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7]/[CH:6]=[CH:5]\[C:4]([OH:21])=[O:3])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14196833HCID 14196833, compound

Product 1

HCID 14347236HCID 14347236, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (Z)-5,5-diphenyl-2,4-pentadieneoic acid ethyl ester (3.5 g) in methanol (20 mL) was treated with a 4N potassium hydroxide solution (5 mL) and the mixture was stirred at reflux for 30 minutes. Most of the methanol was removed under reduced pressure, then the residual solution was poured over ice containing 3N hydrochloric acid (10 mL). The resulting solid was collected by filtration, washed with water, dried and crystallized from dichloromethane-hexane to furnish 3.05 g of (Z)-5,5-diphenyl-2,4-pentadienoic acid mp 175°-176.5° C.

Workup

  1. temperatureat reflux for 30 minutes
  2. customMost of the methanol was removed under reduced pressure
  3. additionthe residual solution was poured over ice containing 3N hydrochloric acid (10 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-f67ed30e46024b37b2fd0cba98072232
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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