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

HRID 485151

Reaktionsgleichung

Reaktionsgleichung von HRID 485151
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2a8023f98b2841b287ce88a35ef8fafc
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04535183

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