Sodium Chloride → 2-Hydroxy-5-iodo-3-methylbenzoic acid

HRID 1916564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916564
Cl[O-].[Na+].[OH:4][C:5]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8].[Na+].[I-:17].[OH-].[Na+].[Na+].[Cl-]>CO.O.C(Cl)Cl>[OH:4][C:5]1[C:14]([CH3:15])=[CH:13][C:12]([I:17])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Komponenten

9

Edukt 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl esterHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 159086852-Hydroxy-5-iodo-3-methylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

14.9 mL (24.1 mmol) sodium hypochlorite solution (10 percent by weight in water) is added dropwise to a solution of 4.0 g (24.1 mmol) methyl 2-hydroxy-3-methyl-benzoate, 3.6 g (24.1 mmol) NaI, 0.96 g (24.1 mmol) NaOH in 100 mL MeOH at −5° C. over 40 min. The reaction is stirred for 30 min at −5° C. and 5 days at RT. The solvent is eliminated i.vac. and the residue is taken up in 80 mL water and 50 mL DCM. After the organic phase has been saturated with NaCl it is extracted twice with DCM. The combined organic extracts are filtered and the solvent is eliminated i.vac. The product is further reacted without any more purification.

Aufarbeitung

  1. extractionis extracted twice with DCM
  2. filtrationThe combined organic extracts are filtered
  3. customThe product is further reacted without any more purification

Quellen und Nachweise

ORD-Eintrag
ord-638b86c89d4a4a29b79d882457ac8a43
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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