Potassium Cyanide → (2-(Methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile

HRID 253255Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])[C:4]=1[O:14][CH3:15].[C-:16]#[N:17].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:15][O:14][C:4]1[C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][C:16]#[N:17]

Participants

Conditions

Temperature: 60 °C

Procedure

1-(Chloromethyl)-2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}benzene (0.33 g, 1.4 mmol) was dissolved in N,N-dimethylformamide (2 mL) followed by the addition potassium cyanide (0.12 g, 1.6 mmol), and the resulting mixture was heated at 60° C. for 18 hours. After cooling to room temperature, it was diluted with ethyl acetate (50 mL), washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (50% ethyl acetate/hexanes) to provide (2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (0.17 g, 0.76 mmol, 54% yield). 1H NMR (400 MHz, CDCl3): 7.03-7.00 (d, d, 1H), 6.95-6.89 (m, 2H), 4.16-4.14 (m, 2H), 3.94 (s, 3H), 3.79-3.77 (m, 2H), 3.70 (s, 2H), 3.44 (s, 3H).

Workup

temperatureAfter cooling to room temperature
washwashed with water and brine (20 mL each)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give an oily residue which
customwas purified by flash chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-4619461f5b344fdbae0a49b6b7b4042f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872014B2

Reaction notes

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