Water → [4-(2-Benzyloxybenzyl)phenyl]acetonitrile

HRID 1247724Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:24]#[N:25].[K+].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][C:24]#[N:25])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(2-benzyloxybenzyl)benzyl chloride (0.66 g) in N,N-dimethylformamide (20 mL) was added potassium cyanide (0.40 g), and the mixture was stirred at 60° C. for 18 hours. The reaction mixture was cooled to ambient temperature, and water was added thereto. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1–3/1) to give [4-(2-benzyloxybenzyl)phenyl]acetonitrile (0.54 g).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
extractionThe resulting mixture was extracted with ethyl acetate
washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1–3/1)

Sources & evidence

ORD record: ord-fc07444f00054455b07a6e9a85344dd4
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129381B2

Reaction notes

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