2-Methyl-2-butene → 2-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzoic acid

HRID 1158461

Reaktionsgleichung

Reaktionsgleichung von HRID 1158461
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:6][C:3]=1[CH:4]=[O:5].C([OH:22])(C)(C)C.C(Cl)Cl.CC(=CC)C.[O-]Cl=O.[Na+]>O.CC#N.CC#N.O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:6][C:3]=1[C:4]([OH:22])=[O:5]

Komponenten

8

Edukt 4

HCID 105532-Methyl-2-buteneHCID 18914702t-Butanol dichloromethaneHCID 23668197Sodium ChloriteHCID 592240102-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzaldehyde

Produkt 1

HCID 595122372-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel2×HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-methoxy-5-(3-methoxy-propoxy)-benzaldehyde (1.08 g, 3.55 mmol) in a 3:1 mixture of tert-butanol/CH2Cl2 (20 mL) is added 2-methyl-2-butene (0.74 g, 5.32 mmol), followed by dropwise addition of a solution of NaClO2 (0.67g, 7.10 mmol) and NaH2PO4 (0.67 g, 4.26 mmol) in water (14 mL) over 15 min at room temperature, and stirring is continued overnight. The reaction mixture is poured into ice/saturated aqueous NaHCO3 solution, the water phase is washed with AcOEt. The ice-cold aqueous layer is acidified with HCl 37% to form a white precipitate which is filtered off, washed with ice-cold water and dried in vacuo. The compound is obtained as white solid. MS: 273.0 [M−H]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 3.25 min. 1H-NMR (CDCl3): δ 1.96 (m, 2H), 3.25 (s, 3H), 3.47 (m, 2H), 3.85 (s, 3H), 4.03 (m, 2H), 7.10 (s, 1H), 7.39 (s, 1H) ppm.

Aufarbeitung

  1. additionThe reaction mixture is poured into ice/saturated aqueous NaHCO3 solution
  2. washthe water phase is washed with AcOEt
  3. customto form a white precipitate which
  4. filtrationis filtered off
  5. washwashed with ice-cold water
  6. customdried in vacuo
  7. customThe compound is obtained as white solid
  8. custom3.25 min

Quellen und Nachweise

ORD-Eintrag
ord-c8ed2c8768744fa8aef40a50a880b3f2
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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