1-Methoxy-2-(2-methylprop-1-en-1-yl)benzene → o-Isobutylanisole

HRID 25822Notes

Reaction equation

HRID 25822 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[C:10]([CH3:12])[CH3:11]>CCO.[Pd]>[CH2:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 1

HCID 124062791-Methoxy-2-(2-methylprop-1-en-1-yl)benzene

Product 1

HCID 3045304o-IsobutylanisoleYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(2-methoxyphenyl)-2-methylpropene (9a) (3.37 g, 20.8 mmol) and 10% Pd/C (300 mg) in 100 ml of anhydrous EtOH at rt was hydrogenated at 60 psi until complete conversion was determined by GC/MS (9 h). The reaction mixture was filtered through celite and concentrated in vacuo to yield 2.87 g of a clear oil (84%): 1H NMR (500 MHz, CDCl3) δ 0.90 (d, J=6.6 Hz, 6H), 1.92 (m, 1H), 2.49 (d, J=7.1 Hz, 2H), 3.82 (s, 3H), 6.88 (m, 2H), 7.10 (d, J=8.9 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 22.55, 28.64, 39.43, 55.22, 110.27, 120.07, 126.80, 130.22, 130.80, 157.70; HRMS (EI) Calcd for C11H16O: 164.1201. Found 164.1207.

Workup

  1. customat rt
  2. customwas determined by GC/MS (9 h)
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d0c792e5d98470c8f2300275f447e31
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Reaction notes

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