Hydrochloric Acid → HCID 66991578, compound

HRID 556279Notes

Reaction equation

HRID 556279 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[CH:8]=O.[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[CH3:16].Cl>C(O)C.O.[OH-].[K+]>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[CH:8]=[CH:16][C:15](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 86235056HCID 86235056, compound

Product 1

HCID 66991578HCID 66991578, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideSolventHCID 19096565Water ethanolSolvent

Procedure

3-(3-fluoro-4-formyl-phenyl)-acrylic acid (500 mg, 2.57 mmol) was dissolved in ethanol/water (1:1, 10 ml) and 1.7M KOH (3 ml). To the resulting solution was added acetophenone (0.3 ml, 2.57 mmol). The mixture was stirred at room temperature overnight then acidified with 10% HCl and extracted with EtOAc. The organic layer was dried over Na2SO4 and the solvent was evaporated under vacuo. The crude product was triturated in EtOAc and filtered to give 560 mg of 3-[3-fluoro-4-(3-oxo-3-phenyl-propenyl)-phenyl]-acrylic acid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated under vacuo
  4. customThe crude product was triturated in EtOAc
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4b36240816474d298a65eb631a3f8e6f
Source dataset
uspto-grants-2011_11
Patent number
US08058273B2

Reaction notes

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