Tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate → Tert-butyl 2-methyl-4-(1-phenylethyl)benzoate

HRID 1501199Notes

Reaction equation

HRID 1501199 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH2:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[H][H]>[Pd].C1(C)CCC(C(C)C)C(O)C1>[CH3:1][C:2]1[CH:14]=[C:13]([CH:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5]

Participants

5

Reactant 2

HCID 89580861Tert-butyl 2-methyl-4-(1-phenylvinyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 89581013Tert-butyl 2-methyl-4-(1-phenylethyl)benzoateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1254MentholSolvent

Procedure

The tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate (1.8 g, 6.1 mmol), palladium 10% on carbon (0.61 mmol, 700 mg) and 30 mL menthol was stirred at room temperature under the atmosphere of hydrogen (4 atmosphere) for 24 hours. Then mixture was filtered, the filtrate was concentrated to give tert-butyl 2-methyl-4-(1-phenylethyl)benzoate (1.6 g, 90%) product. 1H-NMR (300 MHz, CD3OD) δ 7.67 (d, J=8.1 Hz, 1H), 7.24-7.08 (m, 7H), 4.02 (m, 1H), 2.48 (s, 3H), 1.59-1.61 (s, 9H).

Workup

  1. filtrationThen mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c6b5dc49e3c4bb2a670b6b461c99dd0
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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