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

HRID 17892Notes

Reaction equation

HRID 17892 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 70.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Oxo-3-m-tolylpropionate ethyl ester (1 g, 4.84 mmol) was dissolved in benzene, and benzaldehyde (0.51 g, 4.84 mmol), acetic acid (0.15 g, 2.49 mmol) and piperidine (0.06 g, 0.8 mmol) were added thereto. The mixture was refluxed for 4 hours. After the reaction was completed, the organic layer extracted with ethyl acetate/saturated sodium chloride/sodium bicarbonate was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 2-(3-methylbenzoyl)-3-phenylacrylate ethyl ester (1 g, yield 70%).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. extractionthe organic layer extracted with ethyl acetate/saturated sodium chloride/sodium bicarbonate
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-5fe63f61b2d2449bbe145dbec5d40181
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Reaction notes

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