Potassium Iodide → HCID 11148053, compound

HRID 1955149Notes

Reaction equation

HRID 1955149 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Br)[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[CH2:13]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[CH:12]=[CH2:11]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 72132,4-DihydroxybenzaldehydeHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 11148053HCID 11148053, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,4-dihydroxybenzaldehyde (15 g), allyl bromide (9.6 ml), potassium carbonate (15.4 g), potassium iodide (18.5 g) and tetra-n-butylammonium bromide (3.59 g) in methyl ethyl ketone (200 ml) was heated at reflux for 1 hour. The reaction mixture was filtered and evaporated. The residue was partitioned between ethyl acetate (100 ml) and water (100 ml). The organic phase was evaporated and the residual oil (20 g) purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (95:5, v/v). Fractions homogenous in the required product were combined and evaporated to give the title compound (13.8 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. customevaporated
  5. customThe residue was partitioned between ethyl acetate (100 ml) and water (100 ml)
  6. customThe organic phase was evaporated
  7. customthe residual oil (20 g) purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (95:5
  8. customevaporated

Sources & evidence

ORD record
ord-78c076e9d94246a59775821510fbcd4d
Source dataset
uspto-grants-2000_09
Patent number
US06124343

Reaction notes

Loading…