Potassium Hydroxide → HCID 14347308, compound

HRID 2232745Notes

Reaction equation

HRID 2232745 reaction equation
C([O:3][C:4](=[O:22])/[C:5](/[CH3:21])=[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.O>[C:9]1([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7]/[CH:6]=[C:5](\[CH3:21])/[C:4]([OH:22])=[O:3])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86742560HCID 86742560, compound2×

Product 1

HCID 14347308HCID 14347308, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

As in the Example 99. a solution of 3,3-diphenyl-2-propenal (2.08 g) in ethanol (25 mL) was reacted with (carbethoxyethylidene)triphenylphosphorane (4.0 g) for 30 minutes at room temperature. The reaction was worked up in the usual manner to give 2.8 g of (E)-5,5-diphenyl-2-methyl-2,4-pentadienoic acid ethyl ester as the sole product. The crude ester (2.8 g) in methanol (25 mL) was treated with 2N potassium hydroxide (10 mL) and the mixture was heated at reflux until the oil dissolved, then it was cooled and left at ambident temperature overnight. The reaction was diluted with water (20 mL) and most of the methanol was removed under reduced pressure. The solution was acidified with 2N hydrochloric acid (12 mL) and the resulting solid was recovered by filtration, washed with water and dried. The crude acid was triturated with hot hexane to furnish 2.08 g of (E)-5,5-diphenyl-2-methyl-2,4-pentadienoic acid, mp 184°-186° C. A sample was crystallized from 2-propanol to afford the analytical specimen, mp 185°-186.5° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux until the oil
  3. dissolutiondissolved
  4. temperatureit was cooled
  5. customwas removed under reduced pressure
  6. filtrationthe resulting solid was recovered by filtration
  7. washwashed with water
  8. customdried
  9. customThe crude acid was triturated with hot hexane

Sources & evidence

ORD record
ord-766c98a88b4e4946b17afa2dbe6d5dbc
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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