Potassium Hydroxide → HCID 14347235, compound

HRID 1110495Notes

Reaction equation

HRID 1110495 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 14196832Ethyl (2E)-5,5-diphenyl-2,4-pentadienoate

Product 1

HCID 14347235HCID 14347235, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-5,5-diphenyl-2,4-pentadieneoic acid ethyl ester (15 g) in methanol (80 mL) was treated with a 4N Potassium hydroxide solution (20 mL) and the mixture was stirred at reflux for 45 minutes. Most of the methanol was removed under reduced pressure, then the residual solution was poured over ice containing 3N hydrochloric acid (30 mL). The resulting solid was collected by filtration washed with water and dried. Crystallization of the crude material from 2-propanol furnished 11.7 g of (E)-5,5-diphenyl-2,4-pentadienoic acid mp 193°-194° C. Recrystallization from the same solvent did not affect the melting Point. Anal. Calculated for C17H14O2 : C, 81.57: H, 5.63 Found: C, 81.43; H. 5.81.

Workup

  1. temperatureat reflux for 45 minutes
  2. customMost of the methanol was removed under reduced pressure
  3. additionthe residual solution was poured over ice containing 3N hydrochloric acid (30 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. customCrystallization of the crude material from 2-propanol

Sources & evidence

ORD record
ord-71f78bd4e5084a6a9bdf8452aafef985
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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