Potassium Iodide → (3,4-Diethoxyphenyl)acetonitrile

HRID 2204924Notes

Reaction equation

Br[CH2:2][CH3:3].[OH:4][C:5]1[CH:6]=[C:7]([CH2:12][C:13]#[N:14])[CH:8]=[CH:9][C:10]=1O.[C:15](=[O:18])([O-])[O-].[K+].[K+].[I-].[K+].[CH3:23]N(C)C=O>O>[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([CH2:12][C:13]#[N:14])[CH:8]=[CH:9][C:10]=1[O:18][CH2:15][CH3:23])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

15.44 g (140 mmol) of bromoethane and 8.95 g (59 mmol) of 2-(3,4-Dihydroxyphenyl)-acetonitrile are dissolved in 120 mL of N,N-dimethylformamide. 19.39 g (140 mmol) of potassium carbonate and 0.97 g (6 mmol) of potassium iodide are added to the mixture and the resulting suspension is heated to 80° C. After 6 h the reaction mixture is cooled down to at least 30° C. Pour the suspension on 200 mL of icy water, stir for ca. 20 min and filter off. Digest the solid in 120 mL of water, neutralize with hydrochloric acid 25% stir for 30 min. The precipitate is filtered off, washed with water and dried under vacuum at r40° C. 4.72 g of 2-(3,4-diethoxyphenyl)-acetonitrile are obtained as a white powder (39.3% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.

Workup

temperatureAfter 6 h the reaction mixture is cooled down to at least 30° C
filtrationfilter off
stirringstir for 30 min
filtrationThe precipitate is filtered off
washwashed with water
customdried under vacuum at r40° C

Sources & evidence

ORD record: ord-afcabcef79f84dc28edad7de6e13ca2b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09366906B2

Reaction notes

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