Ethyl 3-(2,4-difluorophenyl)prop-2-enoate → Ethyl 3-(2,4-difluorophenyl)propanoate

HRID 974392Notes

Reaction equation

HRID 974392 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[H][H]>C(O)C.[Ni]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 53395691Ethyl 3-(2,4-difluorophenyl)prop-2-enoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19986449Ethyl 3-(2,4-difluorophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

42.4 g (0.20 mol) of ethyl 3-(2,4-difluorophenyl)-2-propenoate are dissolved in 400 ml of ethanol, 4 g of Raney nickel in ethanol are added, and the mixture is hydrogenated at 20°-25° C. using hydrogen gas. When the theoretical amount of hydrogen has been taken up, the solution is filtered and evaporated on a vacuum rotary evaporator. 41.4 g of a pale brown oil which is subjected to fractional distillation at 120° C. in vacuo (20 mbar) are obtained. 33 g (77% of theory) of a colourless oil are obtained.

Workup

  1. customis hydrogenated at 20°-25° C.
  2. filtrationthe solution is filtered
  3. customevaporated on a vacuum rotary evaporator
  4. distillation41.4 g of a pale brown oil which is subjected to fractional distillation at 120° C. in vacuo (20 mbar)
  5. customare obtained
  6. custom33 g (77% of theory) of a colourless oil are obtained

Sources & evidence

ORD record
ord-0b9eae936bac40c1b82f970399fd648b
Source dataset
uspto-grants-1991_11
Patent number
US05068371

Reaction notes

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