Hexamethylenetetramine → Methyl 4-formyl-3-methoxybenzoate

HRID 501811

Reaktionsgleichung

Reaktionsgleichung von HRID 501811
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7].BrN1C(=[O:20])CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C1N2CN3CN(C2)CN1C3>C1C=CC=CC=1.C(O)(=O)C.O>[CH:13]([C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1])=[O:20]

Komponenten

8

Edukt 4

HCID 4101HexamethylenetetramineHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl ester

Produkt 1

HCID 10631650Methyl 4-formyl-3-methoxybenzoateAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

2.50 g of methyl 3-methoxy-4-methylbenzoate was dissolved in 25 mL of benzene, to which 2.72 g of N-bromosuccinimide and 0.23 g of 2,2′-azobisisobutyronitrile were successively added at room temperature, and this solution was stirred for one hour while heating it under reflux. After 3.90 g of hexamethylenetetramine dissolved in 7.8 mL of acetic acid and 7.8 mL of water was added dropwise to the reaction mixture, benzene was distilled out therefrom, and then the mixture was stirred for one hour while heating it under reflux. The reaction mixture, which was cooled to room temperature, was added to a mixture of chloroform and water and then adjusted to pH 7 with a 20% aqueous solution of sodium hydroxide, and the organic phase was separated therefrom. After the resultant organic phase was successively washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1] to yield 1.74 g of methyl 4-formyl-3-methoxybenzoate as white solid.

Aufarbeitung

  1. additionwere successively added at room temperature
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. distillationwas distilled out therefrom, and then the mixture
  5. stirringwas stirred for one hour
  6. temperaturewhile heating it
  7. temperatureunder reflux
  8. additionwas added to a mixture of chloroform and water
  9. customthe organic phase was separated
  10. washAfter the resultant organic phase was successively washed with water
  11. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled out under reduced pressure
  13. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1]

Quellen und Nachweise

ORD-Eintrag
ord-a3ef6e1c4ac3432e90d3632acd088c9b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772285B2

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