Methyl 2-ethenyl-4-methylbenzoate → Methyl 2-ethyl-4-methylbenzoate

HRID 514517Notes

Reaction equation

HRID 514517 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[CH2:2]>[Pd].CO>[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

4

Reactant 1

HCID 21779699Methyl 2-ethenyl-4-methylbenzoate

Product 1

HCID 68288774Methyl 2-ethyl-4-methylbenzoateYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Charged compound methyl 2-ethenyl-4-methylbenzoate (773 mg, 4.42 mmol), Pd/C (100 mg) and methanol (14 mL) to a flask, the mixture was then purged with H2, and stirred at room temperature overnight. It was then filtered, filtrated concentrated to give the title compound (646 mg, 83%). 1H NMR (300 MHz, CDCl3): δ 1.22 (3H, t, J=7.5 Hz), 2.36 (3H, s), 2.95 (2H, q, J=7.5 Hz), 3.87 (3H, s), 7.04 (1H, d, J=8.1 Hz), 7.07 (1H, s), 7.78 (1H, d, J=8.1 Hz).

Workup

  1. customthe mixture was then purged with H2
  2. filtrationIt was then filtered
  3. filtrationfiltrated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21e32074b8a14656bab1b6025c452875
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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