Tert-butyl 3-(4-cyano-3-methylphenyl)acrylate → Tert-butyl 3-(4-cyano-3-methylphenyl)propanoate

HRID 219561Notes

Reaction equation

HRID 219561 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][C:4]=1[CH3:18])#[N:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])=[CH:5][C:4]=1[CH3:18])#[N:2]

Participants

5

Reactant 2

HCID 68649265Tert-butyl 3-(4-cyano-3-methylphenyl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68649344Tert-butyl 3-(4-cyano-3-methylphenyl)propanoateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 3-(4-cyano-3-methylphenyl)acrylate obtained in step 1, (5.3 g) in ethyl acetate (50 mL) was added palladium on carbon (500 mg) and the mixture was placed under a pressure of 3 kg of hydrogen for 3 h at RT. The catalyst was removed by filtration and the filtrate was concentrated under vacuum to afford the title compound as white solid (5.2 g, 98%). 1H-NMR (CDCl3, 400 MHz) δ 7.51-7.53 (1H, d), 7.16 (1H, s), 7.10-7.12 (1H, d), 2.91-2.94 (2H, t), 2.53-2.57 (2H, t), 2.52 (3H, s), 1.42 (9H, s). LC/MS: 246.0 (M+H)+. HPLC (Method C) Rt 3.23 min (Purity: 96.2%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-b829134f99034e71943095a307e96f0d
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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