Potassium Hydroxide → HCID 14347236, compound

HRID 1110494Notes

Reaction equation

HRID 1110494 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. Anal. Calculated for C17H14O2 : C, 81.57; H, 5.63 Found: C, 81.51; H. 5.77.

Workup

  1. temperatureat reflux for 30 minutes
  2. customMost of the methanol was removed under reduced pressure
  3. additionThen the 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-33c57ffe91e64f3c85a3c21dc7ab31e6
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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