2-Methyl-2-butene → 3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoic acid

HRID 1242384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242384
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].CC(=CC)C.Cl([O-])=[O:24].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[CH2:1]([O:3][C:4]([C:5]([CH3:7])([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:15]([OH:24])=[O:16])[CH3:6])=[O:17])[CH3:2]

Komponenten

7

Edukt 4

HCID 105532-Methyl-2-buteneHCID 18766496Ethyl 2-(3-formylphenoxy)-2-methylpropanoateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Produkt 1

HCID 219357143-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoic acidAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

3.33 g (14.1 mmol) of 2-(3-formyl-phenoxy)-2-methyl-propionic acid ethyl ester (example 55A])] was dissolved in 60 ml of tert.-butanol; 7.5 ml (70.5 mmol) of 2-methyl-2-butene was added, followed by a solution of 4.14 g (36.6 mmol) of sodium chlorite and 3.30 g (21.1 mmol) of sodium dihydrogen phosphate in 35 ml of water. After 2 hours, the reaction mixture was poured into crashed ice/EtOAc and extracted twice with EtOAc; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by recrystallisation from EtOAc/heptane to give 3.19 g of the title compound as colorless solid.

Aufarbeitung

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by recrystallisation from EtOAc/heptane

Quellen und Nachweise

ORD-Eintrag
ord-c57ca1e050fa4e7db2daabf4f834cf49
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115611B2

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