Tert-butyl 4-(1-phenylvinyl)benzoate → 1,1-Dimethylethyl 4-(1-phenylethyl)benzoate

HRID 1501024Notes

Reaction equation

HRID 1501024 reaction equation
[C:1]1([C:7]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CO>[C:1]1([CH:7]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[CH:20][CH:21]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 15454427Tert-butyl 4-(1-phenylvinyl)benzoate

Product 1

HCID 895805681,1-Dimethylethyl 4-(1-phenylethyl)benzoateYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of tert-butyl 4-(1-phenylvinyl)benzoate (0.59 g, 2.1 mmol) and palladium on carbon (10%, 100 mg) in methanol (20 mL) was stirred at 20° C. under hydrogen atmosphere (4 atm) for 24 hours. Once the start material has been consumed, the resultant mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give tert-butyl 4-(1-phenylethyl)benzoate (500 mg, 84%). 1H NMR (300 MHz, CD3OD): δ 7.85 (d, J=4.8 Hz, 2H), 7.30-7.15 (m, 7H), 4.19-4.16 (m, 1H), 1.61 (d, J=7.2 Hz, 3H), 1.50 (s, 9H).

Workup

  1. customOnce the start material has been consumed
  2. filtrationthe resultant mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto give a residue
  5. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-9eb21a7beca2475aabddb0d8fc93fd12
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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