Benzene → 1-(4-Methoxyphenyl)cyclohexanecarbonitrile

HRID 2375203

Reaction equation

HRID 2375203 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[H-].[Na+].C1C=CC=CC=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:10]#[N:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 986291-(4-Methoxyphenyl)cyclohexanecarbonitrileYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxyphenylacetonitrile (E1) (1.002 g, 6.8 mmol) and 1,5-dibromopentane (1.886 g, 8.2 mmol) in dry dimethylformamide (15 ml) at ice bath temperature slowly (ca. 2-3 minutes) a 60% suspension of NaH in mineral oil (0.579 g, 14.4 mmol) was added. The obtained reaction mixture was stirred for 15 minutes at ice bath temperature and for 1.5 hours at room temperature, then the contents were poured into benzene (75 ml). The mixture was successively washed with water (3×75 ml), brine (25 ml), and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with petroleum ether-ethyl acetate (5:1) as eluent to give the title compound (0.924 g, 63%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.00-2.28 (10H, m); 3.81 (3H, s); 6.90 (2H, d, J=9.0 Hz); 7.40 (2H, d, J=9.0 Hz).

Workup

  1. customThe obtained reaction mixture
  2. waitfor 1.5 hours at room temperature
  3. washThe mixture was successively washed with water (3×75 ml), brine (25 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silicagel (50 g) with petroleum ether-ethyl acetate (5:1) as eluent

Sources & evidence

ORD record
ord-26ab8c81a5074ccb88c43aedc062d545
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Linked notes

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