Acrylonitrile → 3-(2,3-Dihydrobenzofuran-5-yloxy)propionitrile

HRID 233477Notes

Reaction equation

HRID 233477 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[C:11](#[N:14])[CH:12]=[CH2:13]>CO>[O:9]1[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:13][CH2:12][C:11]#[N:14])=[CH:10][C:6]=2[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 111263112,3-Dihydro-5-hydroxybenzo(b)furan

Product 1

HCID 229113523-(2,3-Dihydrobenzofuran-5-yloxy)propionitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40.8 g of 2,3-dihydro-5-hydroxybenzofuran (the synthesis of which is described in Synthesis 1988, 950-952), 3 ml of a 40% solution of Triton B in methanol and 200 ml of freshly distilled acrylonitrile are mixed at room temperature. The mixture is heated at reflux for 46 hours, then the acrylonitrile is evaporated off as far as possible. The residue is taken up in ethyl acetate, washed with 2N sodium hydroxide solution, N hydrochloric acid and water. The organic phase, dried over magnesium sulphate, is concentrated in vacuo, and then the residue is recrystallised from 300 ml of isopropanol to yield 38 g of the desired compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 46 hours
  3. customthe acrylonitrile is evaporated off as far as possible
  4. washwashed with 2N sodium hydroxide solution, N hydrochloric acid and water
  5. dry with materialThe organic phase, dried over magnesium sulphate
  6. concentrationis concentrated in vacuo
  7. customthe residue is recrystallised from 300 ml of isopropanol

Sources & evidence

ORD record
ord-2a7e4a46a8ef4b418e4b9bddd3ee5125
Source dataset
uspto-grants-1997_01
Patent number
US05593989

Reaction notes

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