Methyl 2-[2-(4-fluorophenyl)ethenyl]-5-methoxybenzoate → Methyl 2-(4-fluorophenethyl)-5-methoxybenzoate

HRID 1251891Notes

Reaction equation

HRID 1251891 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 53733998Methyl 2-[2-(4-fluorophenyl)ethenyl]-5-methoxybenzoate

Product 1

HCID 18324379Methyl 2-(4-fluorophenethyl)-5-methoxybenzoateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-[2-(4-fluorophenyl)ethenyl]-5-methoxybenzoate (43 g, 150 mmol) in ethyl acetate (3.5L) was stirred with 10% Pd/C (4 g) under an atmosphere of hydrogen (pressure 5 bar), at ambient temperature for 18 hours. The spent catalyst was removed by filtration through a Celite pad, the pad was washed with ethyl acetate and the filtrate evaporated to dryness to give methyl 2-(4-fluorophenethyl)-5-methoxybenzoate (33.8 g, 80% yield).

Workup

  1. customThe spent catalyst was removed by filtration through a Celite pad
  2. washthe pad was washed with ethyl acetate
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-d05351ce0f5a490aab56a68046c051e0
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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