Potassium Cyanide → (3-Cyclopropylmethoxy-4-methoxyphenyl)acetonitrile

HRID 1604427Notes

Reaction equation

HRID 1604427 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([O:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)[CH:4]=1.[C-:16]#[N:17].[K+]>CN(C=O)C.O>[CH:13]1([CH2:12][O:11][C:5]2[CH:4]=[C:3]([CH2:2][C:16]#[N:17])[CH:8]=[CH:7][C:6]=2[O:9][CH3:10])[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 224568464-(Chloromethyl)-2-(cyclopropylmethoxy)-1-methoxybenzene

Product 1

HCID 22456848(3-Cyclopropylmethoxy-4-methoxyphenyl)acetonitrileYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(chloromethyl)-2-(cyclopropylmethoxy)-1-methoxybenzene (7.4 g) in DMF (68 ml) was stirred at 60° C. A mixture of potassium cyanide (4.26 g) in water (3.4 ml), previously heated to 80° C., was added dropwise. The resulting reaction mixture was stirred for 30 minutes at 60° C. The reaction mixture was cooled, treated with water (47 ml), and extracted with DIPE. The separated organic layer was dried (Na2SO4), filtered, and the solvent was evaporated, yielding 6.2 g (85%) of 3-(cyclopropylmethoxy)-4-methoxybenzeneacetonitrile (interm. 16).

Workup

  1. temperaturepreviously heated to 80° C.
  2. additionwas added dropwise
  3. customThe resulting reaction mixture
  4. stirringwas stirred for 30 minutes at 60° C
  5. temperatureThe reaction mixture was cooled
  6. extractionextracted with DIPE
  7. dry with materialThe separated organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a373fde82e514c5daaf7e7bbffdf488e
Source dataset
uspto-grants-1999_11
Patent number
US05994376

Reaction notes

Loading…