2,5-Dimethylphenol → HCID 2345580, compound

HRID 1376557Notes

Reaction equation

HRID 1376557 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[C:10](#[N:13])[CH:11]=[CH2:12].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO.C(OCC)(=O)C>[C:10]([CH2:11][CH2:12][O:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])#[N:13]

Participants

6

Reactant 3

HCID 72672,5-DimethylphenolHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 2345580HCID 2345580, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 15.0 g of 2,5-dimethylphenol, 16.17 mL of acrylonitrile, and 0.75 mL of Triton-B (a 40% solution of benzyltrimethylammonium hydroxide in methanol) is heated to reflux overnight. The mixture is diluted with ethyl acetate and washed four times with 5% aqueous sodium hydroxide solution, two times with 3N hydrochloric solution, and two times with water. Drying of the organic layer with sodium sulfate, followed by filtration and evaporation provides 17.4 g of 1-(2-cyanoethoxy)-2,5-dimethylbenzene as a brown oil.

Workup

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. washwashed four times with 5% aqueous sodium hydroxide solution, two times with 3N hydrochloric solution, and two times with water
  4. dry with materialDrying of the organic layer with sodium sulfate
  5. filtrationfollowed by filtration and evaporation

Sources & evidence

ORD record
ord-35e8af9904b7477a9967680f5addb490
Source dataset
uspto-grants-1997_09
Patent number
US05663189

Reaction notes

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