Sodium Iodide → HCID 20484345, compound

HRID 647912Notes

Reaction equation

HRID 647912 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[CH:4]([C:3]1[C:6]([O:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 794355-Bromopentanenitrile

Product 1

HCID 20484345HCID 20484345, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxy-6-methoxybenzaldehyde (3.04 g, 0.02 M), 5-bromopentanonitrile (3.81 g, 0.02 M), anhydrous potassium carbonate (2.97 g), sodium iodide (0.12 g) and ethanol (15 ml) were refluxed with stirring for 41/2 hr. The cooled reaction mixture was filtered and the solid washed well with ethanol. The filtrate was evaporated to dryness and the residue partitioned between ether and water. The organic layer was separated and washed with 2 N sodium hydroxide solution water, dried (sodium sulphate) and evaporated to give 5-(2-formyl-3-methoxyphenoxy)pentanonitrile, 2.92 g, 63%, m.p. 71°-72° C. from benzene/petrol.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe solid washed well with ethanol
  4. customThe filtrate was evaporated to dryness
  5. customthe residue partitioned between ether and water
  6. customThe organic layer was separated
  7. washwashed with 2 N sodium hydroxide solution water
  8. dry with materialdried (sodium sulphate)
  9. customevaporated

Sources & evidence

ORD record
ord-3347c8904c604411a2740e5e5d929529
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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