Potassium Cyanide → (3,4-Bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile

HRID 253248Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[C:5]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:4]=1.[C-:19]#[N:20].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:18][O:17][CH2:16][CH2:15][O:14][C:5]1[CH:4]=[C:3]([CH2:2][C:19]#[N:20])[CH:8]=[CH:7][C:6]=1[O:9][CH2:10][CH2:11][O:12][CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(Chloromethyl)-1,2-bis{[2-(methyloxy)ethyl]oxy}benzene (0.65 g, 2.4 mmol) was dissolved in N,N-dimethyl formamide (2 mL) followed by the addition potassium cyanide (0.20 g, 3.1 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-hexane) to provide (3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (0.59 g, 2.2 mmol, 92% yield). 1H NMR (400 MHz, CDCl3): 6.89-6.93 (m, 3H), 4.16-4.13 (m, 4H), 3.78-3.75 (m, 4H), 3.67 (s, 2H), 3.45 (s, 3H), 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-hexane)

Sources & evidence

ORD record: ord-9a13d0e3272246f6b7e8210938fae193
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872014B2

Reaction notes

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