Sodium Iodide → Ethyl 5-(2-formyl-3-methoxyphenoxy)-2,2-dimethylpentanoate

HRID 647916Notes

Reaction equation

HRID 647916 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][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O: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][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 10681333Ethyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 20484344Ethyl 5-(2-formyl-3-methoxyphenoxy)-2,2-dimethylpentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxy-6-methoxybenzaldehyde (3.74 g, 0.025 M), ethyl 5-bromo-2,2-dimethylpentanoate (5.95 g, 0.025 M), anhydrous potassium carbonate (3.72 g), sodium iodide (0.11 g) and ethanol (50 ml) were refluxed with stirring for 18 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 ethyl 5-(2-formyl-3-methoxyphenoxy)-2,2-dimethylpentanoate, 6.46 g, 84%, as an oil.

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-ba950a3d9cd4438db972b5084841b1e3
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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