Acetic Acid → 2-(3-Methylbenzoyl)-3-phenyl acrylic acid ethyl ester

HRID 19533Notes

Reaction equation

HRID 19533 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6](=[O:14])[C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)[CH3:2].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=1)=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8082PiperidineHCID 2760277Ethyl 3-(3-methylphenyl)-3-oxopropanoate

Product 1

HCID 686968932-(3-Methylbenzoyl)-3-phenyl acrylic acid ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Oxo-3-m-tolylpropionic acid-ethyl ester (1 g, 4.84 mmol) obtained in Step 1 was dissolved in benzene, and benzaldehyde, acetic acid (0.15 g, 2.49 mmol) and piperidine (0.06 g, 0.8 mmol) were added thereto, followed by refluxing for 4 hrs. Upon the completion of the reaction, the mixture washed successively with saturated saline and saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 1 g of the titled compound (yield: 70%).

Workup

  1. temperatureby refluxing for 4 hrs
  2. customUpon the completion of the reaction
  3. washthe mixture washed successively with saturated saline and saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-478fe8470a5b43439c7269167f707cf1
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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