Water → HCID 20513506, compound

HRID 1164023Notes

Reaction equation

HRID 1164023 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][C:18]#N.[H-].[Na+].[CH3:22]I.O.C[N:26]([CH3:29])C=O>>[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[C:17]([CH3:18])([CH3:22])[C:29]#[N:26]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20513415HCID 20513415, compound

Product 1

HCID 20513506HCID 20513506, compound

Procedure

A solution of 2-[2-methoxy-3-(o-tolyloxy)phenyl]acetonitrile (5.2 g) in dimethylformamide (10 ml) was added dropwise to a mixture of 50% sodium hydride (1.1 g) and dimethylformamide (20 ml) below 7° C. in 10 minutes and stirred at the same temperature for 30 minutes. Methyl iodide (6.2 g) was added dropwise to the mixture below 7° C. in 15 minutes and stirred at the same temperature for an hour. Chilled water (200 ml) was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with water, aqueous sodium hydrogen sulfite and water successively, dried over magnesium sulfate and then evaporated to give oily 2-[2-methoxy-3-(o-tolyloxy)phenyl]-2,2-dimethylacetonitrile (5.7 g).

Workup

  1. stirringstirred at the same temperature for an hour
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with water, aqueous sodium hydrogen sulfite and water successively
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-24487fae573c434fba0b5ba7bbb22747
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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