Ethyl 3-[3-(4-methylbenzoyl)phenyl]prop-2-enoate → Ethyl 3-[3-(4-methylbenzoyl)phenyl]propanoate

HRID 1285013Notes

Reaction equation

HRID 1285013 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:8])=[CH:3][CH:2]=1.[H][H]>C(OCC)(=O)C.[Ni]>[C:1]1([CH3:22])[CH:2]=[CH:3][C:4]([C:7]([C:9]2[CH:10]=[C:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:19]=[CH:20][CH:21]=2)=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 54412100Ethyl 3-[3-(4-methylbenzoyl)phenyl]prop-2-enoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20251319Ethyl 3-[3-(4-methylbenzoyl)phenyl]propanoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-(4-toluoyl)cinnamate (Example 4) (3.0 g), in solution in ethyl acetate (90 mL) was shaken with hydrogen in the presence of Raney nickel catalyst until slightly more than 1 molar equivalent of hydrogen had been absorbed. After removal of the catalyst by filtration, the residue was dissolved in dichloro-methane (200 mL), barium manganate (14 g) was added and the mixture was stirred at 50° for 2 hours. The filtered solution was evaporated to leave pure ethyl 3-(3-(4-toluoyl)phenyl)propionate as a yellow oil. (A portion hydrolysed with dilute aqueous alcoholic sodium hydroxide gave the corresponding carboxylic acid, m.p. 137°-138.5°).

Workup

  1. customhad been absorbed
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. dissolutionthe residue was dissolved in dichloro-methane (200 mL)
  5. additionbarium manganate (14 g) was added
  6. customThe filtered solution was evaporated

Sources & evidence

ORD record
ord-c19f5d0c23e744e998fecf9f60be6f32
Source dataset
uspto-grants-1986_01
Patent number
US04564685

Reaction notes

Loading…