Hydrochloric Acid → 5,5-Diphenylpenta-2,4-dienoic acid

HRID 1007760Notes

Reaction equation

HRID 1007760 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:9]=[CH:10][C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl.O>C(O)C>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 53936700Ethyl 5,5-diphenylpenta-2,4-dienoate

Product 1

HCID 544100795,5-Diphenylpenta-2,4-dienoic acidYield 94.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5,5-diphenylpenta-2,4-dienoate (3.70 g) was dissolved in ethanol (68 mL), and 1N sodium hydroxide solution (22 mL) was added thereto, followed by stirring at room temperature for 28.5 hours. Subsequently, while the mixture was stirred under ice-cooling, 1N hydrochloric acid was added thereto, and pH of the resultant mixture was adjusted to about 2. The mixture was condensed to a certain volume under reduced pressure. Water was added to the condensed product, and the thus-obtained solid was collected through filtration and washed several times with water, followed by air-drying, to thereby yield 3.16 g of the product of interest (yield 94.9%).

Workup

  1. stirringSubsequently, while the mixture was stirred under ice-
  2. temperaturecooling
  3. customcondensed to a certain volume under reduced pressure
  4. filtrationthe thus-obtained solid was collected through filtration
  5. washwashed several times with water
  6. customby air-drying

Sources & evidence

ORD record
ord-6e6d353a6faf40e2ac23b9967094223b
Source dataset
uspto-grants-2004_09
Patent number
US06797711B2

Reaction notes

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