(E)-tert-butyl 4-styrylbenzoate → Tert-butyl 4-phenethylbenzoate

HRID 1501068Notes

Reaction equation

HRID 1501068 reaction equation
[CH:1](/[C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Pd].CO>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[CH:20][CH:21]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 89581349(E)-tert-butyl 4-styrylbenzoate

Product 1

HCID 89580569Tert-butyl 4-phenethylbenzoateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of (E)-tert-butyl 4-styrylbenzoate (0.1 g, 0.36 mmol), 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 mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give tert-butyl 4-phenethylbenzoate (90 mg, 89%). 1H NMR (300 MHz, CDCl3): δ 7.90-7.89 (m, 2H), 7.27-7.18 (m, 7H), 2.95-2.94 (m, 4H), 1.59 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-3ca2f8221908489d9af13e7367aaf1d7
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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