Isobutylene oxide → Methyl 5-(2-hydroxy-2-methylpropoxy)-2-nitrobenzoate

HRID 467794

Reaktionsgleichung

Reaktionsgleichung von HRID 467794
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:15][C:16]1([CH3:19])[CH2:18][O:17]1.C(=O)([O-])[O-].[K+].[K+].O.P([O-])(O)(O)=O.[Na+]>C(#N)C.O>[OH:17][C:16]([CH3:19])([CH3:18])[CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

7

Edukt 4

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Produkt 1

HCID 70099919Methyl 5-(2-hydroxy-2-methylpropoxy)-2-nitrobenzoateAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-hydroxy-2-nitrobenzoate (0.5 g, 2.54 mmol), 2,2-dimethyloxirane (6.86 ml, 7.61 mmol), potassium carbonate (351 mg, 2.54 mmol) and sodium dihydrogen phosphate monohydrate (350 mg, 2.54 mmol) in acetonitrile (4 ml) and water (0.6 ml) was stirred at 140° (5 bar) in a steel bomb for 6 hr. After cooling to r.t, the mixture was diluted with water, extracted with AcOEt, dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography using a methylenechloride/MeOH gradient to obtain the title compound (200 mg, 29%) as light yellow viscous oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with AcOEt
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-10d865e4ee694388b6ecaffefeee391d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623866B2

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