Benzene → 1-(4-Methoxyphenyl)cyclohexanecarbonitrile

HRID 2375217Notes

Reaction equation

HRID 2375217 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 (2) (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 min.) 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 content was 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 silica gel (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 silica gel (50 g) with petroleum ether-ethyl acetate (5:1) as eluent

Sources & evidence

ORD record
ord-378c7bcaf3644a00a6e45586044f7a40
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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