Sodium Iodide → Ethyl 7-(2-formyl-3-methoxyphenoxy)heptanoate

HRID 485151

Reaction equation

HRID 485151 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][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].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][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 20271544Ethyl 7-(2-formyl-3-methoxyphenoxy)heptanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxy-6-methoxybenzaldehyde (3.04 g, 0.02 M), ethyl 7-bromoheptanoate (4.74 g, 0.02 M), anhydrous potassium carbonate (2.97 g), sodium iodide (0.12 g) and ethanol (27 ml) were refluxed with stirring for 19 hr. The cooled reaction mixture was filtered and the solid washed with ethanol. The filtrate was evaporated to dryness and the residue partitioned between ether (40 ml) and water (40 ml). The organic layer was separated and washed with ZN sodium hydroxide solution, water, dried (sodium sulphate) and evaporated to give ethyl 7-(2-formyl-3-methoxyphenoxy)heptanoate, 4.2 g, 68% as an oil.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe solid washed with ethanol
  4. customThe filtrate was evaporated to dryness
  5. customthe residue partitioned between ether (40 ml) and water (40 ml)
  6. customThe organic layer was separated
  7. washwashed with ZN sodium hydroxide solution, water
  8. dry with materialdried (sodium sulphate)
  9. customevaporated

Sources & evidence

ORD record
ord-2a8023f98b2841b287ce88a35ef8fafc
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Linked notes

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