Sodium Iodide → (+/-)-Ethyl 5-(2-formyl-3-methoxyphenoxy)-2-methylpentanoate

HRID 647914

Reaktionsgleichung

Reaktionsgleichung von HRID 647914
[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][CH:16]([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][CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:5]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 20484352Ethyl 5-bromo-2-methylpentanoate

Produkt 1

HCID 54476439(+/-)-Ethyl 5-(2-formyl-3-methoxyphenoxy)-2-methylpentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Hydroxy-6-methoxybenzaldehyde (3.74 g, 0.025 M), ethyl 5-bromo-2-methylpentanoate (5.58 g, 0.025 M), anhydrous potassium carbonate (3.72 g), sodium iodide (0.11 g) and ethanol (50 ml) were refluxed with stirring for 16 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-methylpentanoate, 5.3 g, 72%, as an oil.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dc1268eab54c499baf511a56a0b49ecf
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410537

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